Chapter-1

HNGU PATAN 1

INTRODUCTION

CHAPTER-1

Chapter-1

HNGU PATAN 2

CHAPTER-1

INTRODUCTION

1.1 Review on Triazine derivatives

The triazine structure is a heterocyclic ring, analogous to the six-membered

benzene ring but with three carbons replaced by nitrogens. The three isomers of

triazine are distinguished from each other by the positions of their nitrogen atoms, and

are referred to as 1,2,3-triazine, 1,2,4-triazine, and 1,3,5-triazine. Other aromatic

nitrogen heterocycles are pyridines with 1 ring nitrogen atom, diazines with 2

nitrogen atoms in the ring and tetrazines with 4 ring nitrogen atoms. Triazines are

weaker bases than pyridine.

The best known 1,3,5-triazine derivative is melamine with three amino

substituents used in the manufacture of resins. Another triazine extensively used in

resins is benzoguanamine. Triazine compounds are often used as the basis for various

herbicides such as cyanuric chloride (2,4,6-trichloro-1,3,5-triazine). Chlorine-

substituted triazines are also used as reactive dyes. These compounds react through a

chlorine group with hydroxyl groups present in cellulose fibres in nucleophilic

substitution, the other triazine positions contain chromophores. Mixtures of Triazines

and water are also used to remove H2S from natural gas.

A series of 1,2,4-triazine derivatives known as BTPs have been considered in

the liquid-liquid extraction community as possible extractants for use in the advanced

nuclear reprocessing of used fuel. BTPs are molecules containing a pyridine ring

bonded to two 1,2,4-triazin-3-yl groups. Triazine-based molecules have been used as

bridging ligands to bind three dinuclear arene ruthenium (or osmium) compounds to

Chapter-1

HNGU PATAN 3

form metallaprisms. S-Triazine derivatives represent an important class of compounds

due to their potential to be biologically active. They are known to be anti-protozoals, [1], anticancer agents, estrogen receptor modulators, antimalarials, cyclindependent

kinase modulators, [2] and antimicrobials. Cyanuric chloride, an inexpensive, easily

available reagent, of low toxicity and less corrosive than other similar reactants, has

been widely used in organic reactions. 1,3,5-triazines (or s-triazines) are a class of

compounds well known for a long time and still continue the object of considerable

interest mainly due to their application in different fields, including the production of

herbicides and polymer photostabilizers. Some 1,3,5-triazines display important

biological properties; for example hexamethylmelamine (HMM) & 2-amino-4-

morpholino-s-triazine are used clinically due to their antitumor properties to treat

lung, breast and ovarian cancer, respectively. [3]

The diverse biological activities

observed for different molecule containing the 1,3,5-triazine unit have been further

explored in order to discover other new potential molecules through the synthesis of

libraries by combinatorial approaches. Certain 1,3,5-triazine derivatives are also used

as chiral stationary phases, for example, the chiral solvating agent for the

determination of enantiomeric excess by NMR spectroscopy and determination of

absolute configuration by circular dichroism.

Thus owing to the above stated importance of this ligand having s-triazine and

8 -hydroxyquinoline (8-HQ) and their systematic literature survey we were interested

to synthesize coordination polymers based on ligands prepared from s-triazine-ether,

5-amino 8-Hydroxyquinoline and various phenol.

I.B.Johns and H. R. Dipietro [4] reported structure of trimer of salicylonitrile,

2,4,6-tris(2-hydroxy phenyl)-s-triazine suggest that it should be coordinate with

divalent tetracoordinate metal ion to form polymeric products.

Chapter-1

HNGU PATAN 4

N

N

N

R

OH OH N

N

N

R

O O

O

M M

R =

Patrick Gamez, Paul de Hoog and Olivier Roubeau [5]

work on Copper(II)

nitrate reacts with the rigid polydentate triple-connecting 2,4,6-(di-pyridin-2-yl-

amino)-[1,3,5]triazine (dpyatriz) ligand in acetonitrile to an unprecedented infinite

molecular ladder in which five-coordinated copper pseudo-dimers are bridged by

nitrate anions and the coordination polymer chains are linked by hexacoordinated

copper ions leading to the formation of large guest cavities

Megumu Munakata and Ming Wen and Yusaku Suenaga [6] work on carbon

and nitrogen coordinated silver (I) polymers of 2,4,6-triphenoxy-1,3,5-triazine. For

the purpose of furthering the understanding of steric structure effects upon

coordination behavior and exploring the possibility of non-planar complexation in the

triazine system for formation of extended polymeric structures, 2,4,6-triphenoxy-

1,3,5-triazine(tpotz) has been reacted with silver(I) perchlorate and

trifluoromethanesulfonate. The crystal structures of [Ag2(tpotz)3(ClO4)2] and

Chapter-1

HNGU PATAN 5

[Ag2(tpotz)2(CF3SO3)2(THF)] have been determined by single-crystal X-ray

diffraction. Tpotz is rich in organic components that can offer potential sites for

complexation, which can be utilized to generate an interesting array of organometallic

compounds with one-dimensional chains.

Patrick Gamez, Paul de Hoog and Martin Lutz[7]

studied on coordination

compounds from 1,3,5-triazine derived multi-directional ligands which useful for

oxidation catalysis. A series of 1,3,5-triazine- and 2,2-dipyridylamine-based ligands

have been prepared and the crystal structure from one of them was solved. The

coordination of these dendritic multi-directional ligands with various metal salts led to

attractive supramolecular architectures.

N

N

N

O

OO

tpotz

CF3SO3

Ag(1)

Ag(1)

CF3SO3

Schematic view of anion coordinated chain

Chapter-1

HNGU PATAN 6

N

N

N

Cl

ClCl

N

N

N

N

ClCl

R1 R1

N

N

N

N

ClCl

R1 R1

N

N

N

N

NCl

R1 R1

R2

R2

N

N

N

N

NCl

R1 R1

R2

R2

N

N

N

N

NN

R1R1

R2

R2

R3

R3

R12NH

R22NH

R32NH

Oo C

25o C

67o C

THF; DIPEA; Ar; 2 hrs

THF; DIPEA; Ar; 12 hrs

THF; DIPEA; Ar; 24 hrs

Differential reactivity of 1,3,5-triazines

N

N

N N

N

N

N

N

N

N

NNN

N

NN

NN

N O

N

N

NH

N

N

N

N

N

N

N

O

N N

NH

N N

N

NN

NN

N N

N NH

O N

N

Ligands prepared and tested in catechol oxidase activity

Chapter-1

HNGU PATAN 7

Yongquin wei, kechen wu and Ria broer [8] work on a polymeric cobalt

compound [Co(DCNT)(H2O)]n with novel topology: Synthesis, structure,

luminescence, and magnetic property. The hydrothermal reaction of Co(NO3)2. 6H2O

and a new designed ligand H2DCNT yields a three-dimensional polymer [Co(DCNT)

(H2O)]n (1), H2DCNT=2,4-bis(4-carboxyphenylamino)-6-diethylamino-1,3,5-

triazine. In the structure [Co(DCNT) (H2O)]n each DCNT2- has three coordination

sites, one nitrogen atom in the triazine ring coordinating to Co(II) and two

carboxylates adopting bridging mode, which make the infinite Co(II) chains array

uniformly and evenly toward crystallographic c-axis. Luminescent and magnetic

properties of [Co(DCNT) (H2O)]n

were also studied.

N

N

N

Cl

ClCl

N

N

N

ClClN N

N NH

NH

N

C2H5

H5C2

COOH

COOH

+ 2 NH(C2H5)2Acetone

00C

N(C2H5)2

4-Amino benzoic acid

450C

The structure and synthetic route of H2

DCNT

Vinod kumar pandey, Sarah Tusi and Zehra Tusi [9]

reported synthesis and

biological activity of substituted 2,4,6-s-triazine derivatives.

N N

N

O

OH

R' R

O

OH

R'

R

O

OH

R

R'

Chapter-1

HNGU PATAN 8

Jignesh P. Raval, Amrita R. Rai and Nilesh H. Patel [10] reported synthesis and

invivo antimicrobial activity of N’-[4(arylamino)-6-(pyridin-2-ylamino)1,3,5-triazin-

2-yl]benzohydrazide. Here, variety of N'-(4-(arylamino)-6-(pyrazin-2-ylamino)-1,3,5-

triazin-2-yl)isonicotinohydrazide, were synthesized by using 2-aminopyridine,

isonicotinic acid hydrazide and cyanuric chloride. And the structures of these

compounds were confirmed by IR, NMR (1H & 13

C) spectral analysis. The newly

synthesized compounds were also evaluated for antimicrobial activity against variety

of bacterial strains and some of these compounds have shown significant antibacterial

and antifungal activities.

N

NN

NNH

NH

NH

NH

O

R

Sonika jain, Anamika Sharma, Meenakshi Agrawal [11]

reported synthesis and

antimicrobial evaluation of some novel trisubstituted s-triazine derivatives based on

isatinimino, sulphonamido and Azacarbazole.

N

NH

N O

R

N NH

N

N

N

NH

S NH

O

O

R'

O

Chapter-1

HNGU PATAN 9

K. N. Sarmah, N. K. Sarmah and Talha V. Patel [12]

studied synthesis,

characterization and antimicrobial studies of certain triazole containing s-triazine

derived compounds.

N

NNNH

N

N

N

NH S

NH

OMe

NH

OR

G. R. Jani, K. B. Vyas and Zudas Franco [13]

reported preparation and

antimicrobial activity of s-triazine hydrazones of 7-hydroxy coumarin.

OO OH

NCH3 NH

N

N

N

Cl

Cl

K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [14]

reported synthesis of novel

s-triazine derivatives as potential antibacterial agents.

N

N

N

R1

R3R2

Chapter-1

HNGU PATAN 10

Compounds R1 R2 R3

1a Dicyclohexylamine N-methyl piperazine -Cl

1b Dicyclohexylamine Monoethanolamine -Cl

2a Benzimidazole 2-chlorophenylthiourea 2-chloro aniline

2b Benzimidazole 4-chlorophenylthiourea 4-chloroaniline

2c Benzimidazole 4-chlorophenylthiourea 4-fluoroaniline

2d Benzimidazole 3-methylphenylthiourea 3-methyl aniline

K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [15]

reported synthesis and

studies of antifungal activity of 2,4,6-tri substituted 1,3,5-triazines

N

N

N

R1

R3R2

Compounds R1 R2 R3

1a Benztriazole Cyclo hexyl amine Thiourea of m-Toluidine

1b Benztriazole Cyclo hexyl amine Thiourea of O-Toluidine

1c Benztriazole Cyclo hexyl amine Thiourea of p-Toluidine

1d Benztriazole Cyclo hexyl amine Thiourea of p-chloro aniline

1e Benztriazole Cyclo hexyl amine Thiourea of p-anisidine

1f Benztriazole Cyclo hexyl amine Thiourea of p-bromo aniline

2a Benztriazole Benzimidazole Urea of p-chloro aniline

2b Benztriazole Benzimidazole Urea of p-chloro aniline

3a Dicyclo hexyl

amine

Mono ethanol amine -

3b Dicyclo hexyl

amine

N-methyl piperazine -

Chapter-1

HNGU PATAN 11

Firdous D. Khan, Manjusha V. Yadav and Ashok D. Sagar [16]

reported

synthesis, characterization and antimicrobial evaluation of core s-triazine moiety.

N

N

N

O

OO

CHO

CHO

OHC

G. Jagadeesh kumar, H. V. S. sriramkumar bomma, E. srihari and shweta

srivastava [17]

reported synthesis and anticancer activity of some new s-triazine

derivatives.

N

N

N

N

NN

N

N

N

N

NN

N

NCHF2

N

N

N

NNOO

S

N

N

N

N

NH

OHN

N

N

N

NH

NH

NH

MeO

OMe

OMe

Chapter-1

HNGU PATAN 12

Viktor Milata, Ladislav Reinprecht and Juraj Kizlink [18]

reported synthesis

and antifungal efficacy of 1,3,5-triazines.

N NN

NNN

NN

N

N

N

N

N

N

NN

N

N

N

N

N

NN

N N

NN

N

N

N

CH3

CH3

CH3

CH3CH3

CH3N

N

NN

N

N

N

N

N

Ph

Ph

PhPh

Ph

Ph

Anjani solankee, Kishor kapadia, Ana ciric, Marina sokovic and irini

doytchinove [19]

reported synthesis of some new s-triazine based chalcones and their

derivatives as potent antimicrobial drugs.

Chapter-1

HNGU PATAN 13

NN

N

N

N

NH

NH

NH

R

COCH3 N NH2

RCN

N

N

N

NH

NH

NH

N N

R

NH2

N

N

N

NH

NH

NH

Pankaj B. Kaswala, Kishor H. Chikhaliya [20]

design, synthesis and

antimicrobial evaluation of s-triazinyl urea and thio urea derivatives.

O

O

N

N

N

NH

NHO

NH X

R

Carlos A. M. Afonso and co-workers [21]

reported synthesis of 2,4,6-tri-

substituted -1,3,5-triazines.

Nidhi Gautam and O P Chaourasia [22]

isooxazoline and isothiazoline moiety

reported synthesis, characterization and

insecticidal activity of some new s-triazine derivatives of pyrazoline, pyrimidine,

Chapter-1

HNGU PATAN 14

N

N

N

NH

OMe

NH

MeO

NH

CH

OCH

R

Ramachndra S. Hosmane, Mitchell A. Rossman [23]

reported synthesis and

structure of s-triazine.

Loredana Donati and Enzo Funari [24]

reported review on leaching

characteristics of triazines and their degradation products.

Kokila N. Sarmah and Talha V. Patel [25]

reported synthesis, characteristics

and antimicrobial studies of certain s-triazine derived compounds and analogs.

N

N

N

NH

NH

NO

X

NH

NNO

SCH3

R

Chapter-1

HNGU PATAN 15

Edwin M. Smolin and Lorence Rapoport [26]

published book series on s-

triazine and its derivatives. Both author basically from Central research division,

Americal Cyanamid company, Stanford, Connecticut, USA.

Akshay D. Desai, Dharmesh H. Mahajan and Kishor H. Chikhalia [27]

reported

synthesis of novel aliphatic thiourea derivatives containing s-triazine moiety as

potential antimicrobial agents.

R

S

N

N

N

NH

NNH

O

NH

O

NH

S

K. N. Sarmah, N. K. Sarmah and K. B. Kurmi [28]

studied synthesis and studies

of biological evaluation of certain s-triazine derived compounds.

NN

N

N

N

N

N

N

NH

NH

O R

Sweta D. Desai and Arvind G. Mehta [29]

reported design, synthesis and

biological evaluation of various N-substituted piperazine annulated s-triazine

derivatives.

Chapter-1

HNGU PATAN 16

OO

N

N

N

N

O

N

R

OMe

S. G. Kansara, R. D. Pandit and V. G. Bhawe [30]

reported synthesis of some

new ibuprofen derivatives containing heterocyclic moiety like s-triazine and evaluated

for their analgesic activity.

NH

O

CH3

CH3

CH3

R

N

N

N

Cl

NH

O

CH3

CH3

CH3

R

Vineeta sareen, vineeta khatri and Prakash jain [31]

reported synthesis of 2-(6-

fluorobenzothiazole-2’-yl amino)-4-(phenylthioureido)-6-(substituted thioureido)-

1,3,5-triazine as antimicrobial agent.

N

S

N

N

N

NHCSNHR

C6H5NHCSNH NH F

Chapter-1

HNGU PATAN 17

N. sekar, Vikas S. padalkar and Kiran R Phatangare [32]

reported synthesis and

biological evaluation of novel 6-aryl-2,4-di substituted Schiff bases 1,3,5-triazine

derivatives as antimicrobial agents.

ONN

NN

O

N

N

ONN

NN

O

N

N Cl

Cl

ONN

NN

O

N

N OMe

OMe

ONN

NN

O

N

N

Vikas S. padalkar and Vikas S. Patil [33]

reported synthesis and photo physical

properties of fluorescent 1,3,5-triazine styryl derivatives. It was found that the strong

electron acceptor-donor chromophoric system of these compounds showed high

Stoke’s shift and excellent thermal stability. Compounds showed positive

solvatofluorism behaviour from nonpolar to polar solvent. All compounds have good

thermal stability.

Chapter-1

HNGU PATAN 18

ON

NN

O

N

CN

CN

CN

CNO

NN

NO

N

CN

CN

COOEt

COOEt

ON

NN

O

N

CN

CN

Ph

Ph ON

NN

O

N

CN

CN

O2N

O2N

SN

SN

ON

NN

O

N

CN

CN

Divya Karunakaram, Govindarajan R. and Srikanth Jupudi [34]

reported

synthesis and biological evaluation of newer s-triazine derivatives.

N

N

N

NH

ClCl

N X

R

Chapter-1

HNGU PATAN 19

1.2 Brief details on Morpholine containing compounds and its

biological activity

Morpholine [35] is an organic chemical compound having the chemical formula

O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups.

Because of the amine, morpholine is a base; its conjugate acid is called

morpholinium. For example, treating morpholine with hydrochloric acid makes the

salt morpholinium chloride.

NH

O Morpholine is a common additive, in parts per million concentrations, for pH

adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is

used because its volatility is about the same as water, so once it is added to the water,

its concentration becomes distributed rather evenly in both the water and steam

phases. Its pH adjusting qualities then become distributed throughout the steam plant

to provide corrosion protection. Morpholine is often used in conjunction with low

concentrations of hydrazine or ammonia to provide comprehensive all-volatile

treatment chemistry for corrosion protection for the steam systems of such plants.

Morpholine decomposes reasonably slowly in the absence of oxygen at the high

temperatures and pressures in these steam systems.

Morpholine derivatives used as agricultural fungicides in cereals are known as

ergosterol biosynthesis inhibitors

[1] Amorolfine

O

N

Chapter-1

HNGU PATAN 20

Amorolfine (or amorolfin), is a morpholine antifungal drug that inhibits D14

reductase and D7-D8 isomerase [36], which depletes ergosterol and causes ignosterol to

accumulate in the fungal cytoplasmic cell membranes. Marketed as Curanail, Loceryl,

Locetar, and Odenil, amorolfine is commonly available in the form of a nail lacquer,

containing 5% amorolfine as the active ingredient. It is used to treat onychomycosis

(fungal infection of the toe- and fingernails). Amorolfine 5% nail lacquer in once-

weekly or twice-weekly applications has been shown in two studies to be between

60% and 71% effective in treating toenail onychomycosis; complete cure rates three

months after stopping treatment (after six months of treatment) were 38% and 46%.

However, full experimental details of these trials were not available and since they

were first reported in 1992 there have been no subsequent trials. [2] Fenpropimorph

O

N

Fenpropimorph is a morpholine-derived fungicide used in agriculture,

primarily on cereal crops such as wheat. [3] Tridemorph

O

NCH3

Tridemorph is a fungicide used to control Erysiphe graminis. It was developed

by BASF in the 1960s who use the trade name Calixin. The World Health

Organization has categorised it as a Class II "moderately hazardous" pesticide because

it is believed harmful if swallowed and can cause irritation to skin and eyes.

Chapter-1

HNGU PATAN 21

In many commercial drugs also contains Morpholine as a active site which is

medicinally active some of these reported here.

[4] Phenmetrazine

O

NH

Phenmetrazine (Preludin) is a stimulant drug containing a phenethylamine

skeleton, in which the terminal amine is incorporated into a morpholine ring, that was

previously used as an appetite suppressant, but has since been withdrawn from the

market. It was initially replaced by its analogue phendimetrazine which functions as a

prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of abuse

and addiction.

[4] Levofloxacin

N

OO

OH

FN

N

O

Levofloxacin [37] (trade names Levaquin (US), Tavanic (EU), and others) is a

broad spectrum antibiotic of the fluoroquinolone drug class, and the levo isomer of its

predecessor ofloxacin. Its spectrum of activity includes most strains of bacterial

pathogens responsible for respiratory, urinary tract, gastrointestinal, and abdominal

Chapter-1

HNGU PATAN 22

infections, including Gram negative (Escherichia coli, Haemophilus influenzae,

Klebsiella pneumoniae, Legionella pneumophila, Moraxella catarrhalis, Proteus

mirabilis, and Pseudomonas aeruginosa), Gram positive (methicillin-sensitive but not

methicillin-resistant Staphylococcus aureus, Streptococcus pneumoniae,

Staphylococcus epidermidis, Enterococcus faecalis, and Streptococcus pyogenes), and

atypical bacterial pathogens (Chlamydophila pneumoniae and Mycoplasma

pneumoniae). Compared to earlier antibiotics of the fluoroquinoline class such as

ciprofloxacin, levofloxacin exhibits greater activity toward Gram-(+) bacteria but

lesser activity toward Gram-(−) bacteria, especially Pseudomonas aeruginosa.

Levofloxacin and later generation fluoroquinolones are collectively referred to as

"respiratory quinolones" to distinguish them from earlier fluoroquinolones which

exhibited modest activity toward the important respiratory pathogen Streptococcus

pneumoniae.

1.3 Research gaps about the novel 2,4,6-tri substituted-1,3,5-

triazine derivatives.

The usage of most antimicrobial agents is limited, not only by the rapidly

developing drug resistance, but also by the unsatisfactory status of present treatments

of bacterial and fungal infections and drug side-effects [38]

. Therefore, the

development of new and different antimicrobial drugs is a very important objective

and many research programs are directed the design of new antimicrobial agents.

As per the review about the derivatization of various 1,3,5-triazine derivatives,

It is a six-membered heterocycles containing three nitrogen in the ring and its

derivatives have biological activities such as antibacterial, antifungal,

antimycobacterial, anti-inflammatory, analgesic, anticancer, antihypertensive,

anticonvulsant, antiviral, antidepressant, antiasthmatic, diuretic and hypoglycemic.

All these facts were driving force to develop novel 1,3,5-triazine derivatives with

wide structural variation. Thus 1,3,5-triazine derivatives plays pivotal role in

medicinal chemistry.

Chapter-1

HNGU PATAN 23

Here, we are trying to attached a active compounds like 5-(4-Fluoro-phenyl)-

[1,3,4]oxadiazole-2-thiol, 2-Methyl-quinoline-8-amine, 9-ethyl-9H-carbazol-3-amine,

4,5,6,7-Tetrahydro-thieno[2,3-b] pyridine and 4-Amino-N-pyrimidin-2-yl-benzene

Sulfonamide with 1,3,5-triazine, which is already part of existing commercial

pharmaceuticals. Hence, here we are trying to develop new moiety which having good

or better activity then existing pharmaceuticals.

Moreover these substitutions have been studied extensively because of their

ready accessibility, diverse chemical reactivity and broad spectrum of biological

activity. The area in which such a 2,4,6-tri substituted 1,3,5-triazine derivatives has

not been reported so far. Hence, it was thought to undertaken such study.

1.4 Objectives of the present work:

In view of above review, the prime objectives of the present thesis are,

Preparation of various novel 2,4,6-tri substituted-1,3,5-triazine derivatives.

Evaluation of antimicrobial activity of above prepared heterocycles.

Chapter-1

HNGU PATAN 24

1.5 The present work:

According to the above objectives, research work was carried and distributed

into following chapters of the present thesis.

Chapter-2 of the thesis comprises into two sections.

Section-A comprises the details about techniques used for characterization.

Section-B deals with the details about the raw materials used for synthesis. These are

as follow.

(i) Cyanuric chloride,

(ii) Amino oxadiazole,

(iii) 2-Methyl-quinoline-8-amine

(iv) 9-ethyl-9H-carbazol-3-amine

(v) 4,5,6,7-tetrahydrothieno[3,2-b]pyridine

(vi) Sulfapyrimidine

Chapter-3 of the thesis comprises the synthesis and characterization of 2-(4-

flourophenyl-1,3,4-oxadiazoleyl)-5-thio-4-(morpholino)-6-(arylamino)-s-triazine

derivatives.

Chapter-4 of the thesis comprises the synthesis and characterization of N-(9-

Ethyl-9H-carbazol-3-yl)-6-morpholin-4-yl-N’-aryl amine-[1,3,5]triazine-2,4-diamine

derivatives.

Chapter-5 of the thesis comprises the synthesis and characterization of N-(2-

Methyl-quinolin-8-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine

derivatives.

Chapter-1

HNGU PATAN 25

Chapter-6 of the thesis comprises the synthesis and characterization of [4-(5,6-

Dihydro-4H-thieno[2,3-b]pyridin-7-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl-

amine derivatives.

Chapter-7 of the thesis comprises the synthesis and characterization of 4-(4-

Morpholin-4-yl-6-phenylamino-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-

benzenesulfonamide derivatives

All the prepared compounds mentioned in chapters-3 to 7 were screened for

their antimicrobial activity. The common biospecies have been selected. The results

of such study are discussed in chapter-8.

The entire synthetic route is scanned in Scheme 1.1 to 1.5.

Chapter-1

HNGU PATAN 26

N N

N ClCl

Cl N N

N Cl

Cl

O

NN

F

SO

NN

SHF

O

NH

N N

N

Cl

O

NN

F

S N

ONH2

R

N N

NO

NN

F

S N

O

NH

R

+THF / 10% NaHCO3

0-50C

THF / 10% NaHCO3

40-450C

+

Dioxane / 10% NaHCO3

100-1100C

(1)(2) (3)

(4)

(5a-j)

(6a-j)

2,4,6-Trichloro-[1,3,5]triazine 5-(4-Fluoro-phenyl)-[1,3,4]oxadiazole-2-thiol 2,4-Dichloro-6-[5-(4-fluoro-phenyl)

-[1,3,4]oxadiazol-2-ylsulfanyl]-[1,3,5]triazine

Morpholine

2-Chloro-4-[5-(4-fluoro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-6-morpholin-4-yl-[1,3,5]triazine

2-(4-fluoro phenyl-1,3,4-oxadiazoleyl)-5-thio-4-(morpholino)-6(arylamino)-s-triazine derivatives

Where, R = 4-CH3, 4-F, 3-Cl-4-F, 4-NO2, 4-OCH3, 3-CH3, 4-Br, 4-OCOCH3, 3-Cl, 4-Cl

Scheme 1.1

Chapter-1

HNGU PATAN 27

N N

N ClCl

Cl

O

NH

NH2

R

N

NH2

N

NH

N N

N ClCl

N

O

NNH

N

NN

Cl

NH

NO

N

NH

N N

N

R

+THF / 10% NaHCO3

0-50C

THF / 10% NaHCO3

40-450C

+

Dioxane / 10% NaHCO3

100-1100C

(1)(8)

(5a-j)

(10a-j)

2,4,6-Trichloro-[1,3,5]triazine

Morpholine

(7)9-Ethyl-9H-carbazol-3-ylamine (4,6-Dichloro-[1,3,5]triazin-2-yl)-

(9-ethyl-9H-carbazol-3-yl)-amine

(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-(9-ethyl-9H-carbazol-3-yl)-amine

(9)

N-(9-Ethyl-9H-carbazol-3-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine derivatives

Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2

Scheme 1.2

Chapter-1

HNGU PATAN 28

N N

N ClCl

Cl

O

NH

NH2

R

NNH2

CH3

N N

N Cl

Cl

N

NH

CH3

O

N

N N

N

Cl

N

NH

CH3

NH

O

N

N N

N

N

NH

CH3

R

+THF / 10% NaHCO3

0-50C

THF / 10% NaHCO3

40-450C

+

Dioxane / 10% NaHCO3

100-1100C

(1) (12)

(5a-j)

(14a-j)

2,4,6-Trichloro-[1,3,5]triazine

Morpholine

2-Methyl-quinolin-8-ylamine(11)

(4,6-Dichloro-[1,3,5]triazin-2-yl)-(2-methyl-quinolin-8-yl)-amine

(13)(4-Chloro-6-morpholin-4-yl-[1,3,5]-triazin-2-yl)-(2-methyl-quinolin-8-yl)-amine

N-(2-Methyl-quinolin-8-yl)-6-morpholin-4-yl-N'-aryl amine-[1,3,5]triazine-2,4-diamine derivatives

Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2

Scheme 1.3

Chapter-1

HNGU PATAN 29

N N

N ClCl

Cl

O

NH

NH2

R

NH

S

N

N N

N

O

N

S

N

N N

N Cl

Cl

SNH

S

N

N N

N

Cl

O

N

R

+THF / 10% NaHCO3

0-50C

+

Dioxane / 10% NaHCO3

100-1100C

(1)

(16)

(5a-j)

(18a-j)

2,4,6-Trichloro-[1,3,5]triazine (15)

(17)

4,5,6,7-Tetrahydro-thieno[2,3-b]pyridine

7-(4,6-Dichloro-[1,3,5]triazin-2-yl)-4,5,6,7-tetrahydro-thieno[2,3-b]pyridine

7-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-yl)-4,5,6,7-tetrahydro-thieno[2,3-b]pyridine

[4-(5,6-Dihydro-4H-thieno[2,3-b]pyridin-7-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-phenyl-amine derivative

Morpholine

THF / 10% NaHCO3

40-450C

Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2

Scheme 1.4

Chapter-1

HNGU PATAN 30

N N

N ClCl

Cl

O

NH

NH2

R

NH2 S NH

O

O N

N

N N

N NH

Cl

Cl S NH

O

O N

N

N N

N NH

Cl

S NH

O

O N

NO

N

NH

N N

N NH

S NH

O

O N

NO

N

R

+

THF / 10% NaHCO3

40-450C

(1)(20)

(5a-j)

(22a-j)

2,4,6-Trichloro-[1,3,5]triazine

Morpholine

(19)

(21)

4-Amino-N-pyrimidin-2-yl-benzenesulfonamide

4-(4,6-Dichloro-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamide

THF / 10% NaHCO3

0-50C

4-(4-Chloro-6-morpholin-4-yl-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamide

+

Dioxane / 10% NaHCO3

100-1100C

4-(4-Morpholin-4-yl-6-phenylamino-[1,3,5]triazin-2-ylamino)-N-pyrimidin-2-yl-benzenesulfonamidederivatives

Where, R = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2

Scheme 1.5

Chapter-1

HNGU PATAN 31

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Chapter-1

HNGU PATAN 32

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HNGU PATAN 33

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