View
7
Download
0
Category
Preview:
Citation preview
Indian Journal of Chemistry Sect. B: Organic Chemistry including Medicinal Chemistry
VOL. 43B NUMBER 12 DECEMBER 2004
CONTENTS
2623
Papers
Synthesis and characterization of {[(n-Buh Sn(02CCH=CHAr)hOh and crystal structure of {[(n-BuhSn(02CCH=CHPh)hOh
IPC: Int.CL7 C 07 C 13/20
Handong Yin*, Chuanhua Wang & Chunlin Ma
2628 Synthesis of some novel spiro heterocycles
IPC: Int.C1.7 C 07 D 239/00
Z=NH/O/S
V Padmavathi*, B Jagan Mohan Reddy, A Padmaja, K Venugopal Reddy & M Rajagopala Sarma
Ten organotin compounds {[(n-Bu)2Sn (02CCH = CHAr)hO 12 have been synthesized by the reaction of (n-BuhSnO with ArCH=CHC02H in I: I molar ratio. The crystal structure of [[(n-Buh Sn(02CCH = CHPh)hO h is determined by X-ray single crystal diffraction.
A new class of spi ro pyrimidinetriones, thioxopyrimidinediones, pyrazolidinediones and isoxazolinediones are prepared from dihydropyridine/pyran/thiopyran dicarboxylates.
Jl
A~iX;o" Ar' z Ar'
X=O/S
R=HlCH.l
OVO
ArCO~ XCOAr
Ar' z Ar'
X=O/NH
2613
INDIAN J CHEM, 43B (12) 2004
2614
2635
2641
2646
CONTENTS
Synthcsis and mcsomorphic bchaviour of 3-[4-alkyloxyphcnyIJ-5-[3, 4-cthylcnedioxybellZyIJ-2-isoxazolines
IPe: Int.CL7 C 07 026/00
K II Umesha, K M L Rai *, Nagappa & J Mahadeva
Efficient synthesis of 1,2,4-triazolo[4,3-aj[I,8Jnaphthy.-idines using nitrous acid under microwave irradiation
IPe: Int.CL7 C 070249/22
A simple homologous series of 3-[4-alky loxy phenyl] -5-f3,4-methy Icnedi oxybcnzy 1] -2-isoxazol i nes havi ng chiral sourccs havc been sy nthcs ized by thc rcac tion o f aldoximcs with safrole using ch loraminc-T. Thc sy nthcsized compounds cx hibit chiral ncmatic phasc (N*), smectic A (SA) and chiral smcc ti c phases (SC*).
where 11 = 4-14 7
A simple and efficient protoco l for thc synt hes is of I ,2,4-triazolo f 4,3-(/ HI ,S]naphthyridincs using nitrous ac id under mi crowavc irradiati on is dcscribed.
h NaN02 / CH)COOH •
MW NI-IN=CH-Ar
7
K Mogilaiah*, M Prashanthi & K Vidya
Microwave induced synthesis of 3/4-substituted-2-thioxo-/2-oxo-6-thioxo-l ,2,3,4,6,7 -hexahydrothiazolo [4, 5-dJ py.-imidine and thiazole derivatives
IPC: Int.CL7 C 070239/00, 277/00
Vijay V Oabholkar* & Syed Sagir Ahmed
8
3/4-Substitutcd-2-oxo-6- thioxo- I,2,3,4,6,7-hexahydrothiazolof4,5-d] pyrimidinc derivatives 3 , 3/4-substituted-2, 6-dithi oxo- l , 2, 3, 4,6,7 -hexahydrothiazolof4,5-dJpyrimidine 4 and 4,5-substituted thiazolc derivati ves 6 havc been sy nthcsizcd by usi ng MW irrad iation tcchniquc, which g ives bCllcr y ic ld than the conventi onal method.
INOIAN J CHEM , 43B (12) 2()04
2650
2653
2661
CONTENTS
Microwave accelerated Pechmann synthesis of new isoxazolyl coumarins in dry media
A fa st and effici ent sy nthesis of isoxazo lyl coumarins 2 has been performed via the Pechmann react ion by mi crowave irrad iati on on solid support , montmorillonite K-I O, wh ich also acts as lewis acid catalys t. New isoxazolyl coumarin s have been prepared for the first time unde r dry conditi ons using microwave and by conventional method.
IPC: Int.CI.7 C 07 0 311/00
2
E Rajanarendar*, P Ramesh & K Ramu
Synthesis, characterization and electrochemical behaviour of some substituted 2-phenyl-4-(4'arylazophenyl)-3-thioxo-2H,3,4-dihydro-2,4,9,10-tetraazaphenanthren-I-ones
T he electrochemical reduction of so me subst ituted 2-phe nyl-4-( 4' -ary lazophenyl )-3-t hioxo-2H-3, 4' -dihydro-2, 4, 9, IO-tetraazaphe nan threne-l -ones has been studi ed over wide pH range.The kine tie parameters have also been studied.
IPC: Int.C1.7 C 07 0221/10
Pratibha Sharma*, Ashok Kumar, Manisha Sharma & Siya Upadhyay
Qs N-{ n R oCSN-O-N=N-0 ~
N \ j
R = (a) H, (b) 4 '-CI, (e) 4'-OH , (d) 3'- C2Hs
Porcine pancreas lipase catalysed acetylation of ~-eyclodextrin anchored 4-1-butylcyclohexanol
Porc ine pancreas lipase ca tal yzed acetylation of 4 -1-
butylcyc!ohexanol anchored inside ~-cyc lodextrin
cavity gives the highest yie ld of 86.6% with vari ation in Irans/Cis ra tio . IPC: Int.CI 7 C 07 C 13/18
H H t-Uu H H
H H H
H OH
cis-4-I-butyleyc lohexanol
H H t-Uu H H
H H H
H H
Iralls-4-I-buty leyelohexanol
Balaraman Manohara & Soundar Divakar*
"'c,0, PPL .
DCD acetate
I~-BU-h--N-H P~CHJ
~ cis-4-t-buty lcyc lohexy l acetate
Ac, 0, PPL .
DCD acetate
t-Bu~ H~O~CH' H H H g
Iralls-4-I- butylcyc!ohexy l acetate
2615
INDIAN j CHEM, 43B (12) 2004
2616
2666
2670
CONTENTS
Benzopyrans: Part 47- Reactions of 3-(~-dimethylaminoacryloyl)-I-benzopyran-4-one with some nitrogen nucleophiles
fPC: Int.C!.7 C 07 P 311/04
The title pyranone 1 gives a mixture of pyridines 4 and 7 with ammonia, pyridine 5 and pyrazolc 10 with phenylhydrazine, and pyridine N-ox ide 8 with hydroxylamine.
(1(0) :::,... NMe,
R~ - MR Y
:7 N
:::,... I I I
° ° 1 R = H. Me OH ° °
4 Y=H 5 Y = NHPh
(Y°lrl R~NZ ~
o
:::,... I I R :7 I
Chandra Kanta Ghosh*, Sumit Kumar Karak & Amarendra Patra
Synthetic and biological activity evaluation studies on novel isoxazolidincs
IPC: Int.C!.7 C 07 D 261/64 II A 61 P 31104
o-{
° 7 Z = electron pair 8 Z=--O
° N-N Pl·, ......
10
A series of isoxazolidines have been prepared. Some of these compounds exhibit antioxidant and antibacterial activities. Enantioselective deacetylation studies on isoxazolidines using Candida rugosa lipase are also described .
OH o~
xi1' R' C~ 0 R' ,0 CRL> ):y1' I ~ N I ~ N + NN R ~ b R ~ b R 8 b
0 r
xii' CRL ) R' ,0 I ~ N
R ~ b Shubhasish Mukherjee, Raunak, Ashish Dhawan, Poonam, Ashok K Prasad, Carl E Olsen, Ashok L Cholli, William Errington, Hanumantharao G Raj, Arthur C Watterson & Virinder S Parmar*
xYJ:" R' ,0 I ~ N
R ~ b
0 r-
xii' . R .0
+ I "" N
R' ~ b
INDIAN J CHEM, 43B (12) 2004
CONTENTS
2683 Studies on stereoselective synthesis of ethyl anti-4-su bsti tuted phenyl-2-oxo-l ,3-oxazolidine-5-carboxylates and their anti-bacterial activity
IPC: Int.CI.7 C 07 D 263/00 II A 61 P 31104
Ethyl anti-4-substituted phenyl-2-oxo-I,3-oxazolidine-5-carboxylatcs have bcen synthesized stereoselectively from N-Boc-~-amino alcohols by 0-tosylation followed by SN2 cyclization. All the compounds prepared are tested for their in vitro antibacterial activity against S. aureous, E.faecalis and E.faecium.
oJ< 0
HN~O HN~O ~OTOS _E_t3_N_/C_H_3_C-JI:~ (~~--(1(OEt
RN O~~t RN 0
G Madhusudhan, G Om Reddy*, J Ramanatham & P K Dubey
2689 Potential plant growth regulators: Synthesis and activity of new substituted N-(2-benzoyl-4-chlorophenyl)benzamides and N-[4-chloro-2-(a,a-hydroxyphenylmethyl)phenyljbenzamides
IPC: Int.CI.7 C 07 C 233/07
CI
NHC=O
6~1 2 I A R 5 ~ 3
4
7a-1
Jaywant Govind Hatim & Vidya Joshi*
2696 IH NMR spectral studies of some 2,6-diaryl-4-aminothianes
IPC: Int.CI.7 C 07 D 335/02
K Pandiarajan* & A Manimckalai
(±) anti
NaBH
8a-i
IH NMR spectra have been recorded for 4-aminor(2),t(6)-diphenylthiane 5 and epimeric 4-aminothianes 6a-8a and 6b-8b and analysed.
6a-8a 6b-8b
2617
INDIAN J CHEM, 43B (12) 2004
26 18
2700
2702
CONTENTS
Notes
Synthesis of pynlZoline and isoxazoline in triethanolamine medium
IPC: Int.CI. 7 C 07 0261100,231100
3a-c
Nitin N Agrawal* & P A Soni
Synthesis of 2-(collmarin-3-yl)-4-(chromon-3-yl)benzopyrano[ 4,3-b ]pyridines
IPC: Int.CI.7 C 07 0311100
G Jagath Reddy*, C Thirllpathaiah, 0 Latha, K Srinivasa Rao & Md Khalilullah
Reacti ons of chalcones la-u with pheny lhydrazine and hydra7. ine hydrate give pyrazolines 2a-1i and wi th hydroxylamine hydrochloride yield isoxazol ines 3a-c in tri ethanolamine med ium.
TEA E
NHpH.HCI
R,YYR
N-C-CH=CH-o-~ R3 R2 II _.
o la-u
A series of new 2-(coumarin-3-y l)-4-(chromon-3-yl)benzopyrano[4,3-b]pyridines 3a-1 have been prepared from eoumarinoy lmethy lpyridin ium bromide 1 under Kroenke's condit ions.
R,
INDIAN J CHEM, 43B (12) 2004
2705
270S
2713
CONTE TS
A new rout e for the convenient sy nthesis of 3-aminomethyl-3,5,5-trimethyl-cyclohexanol
IPC: Int. C L7 C 07 C 13/1S, 35/00
Satish C Pandey*, Sudhir S Singh, Balaram Patro & Anil C G hosh
A rapid and emcient synthesis of p-casomorphin employing fioc-amino acids and 9-lluorenylmethyl chloroformate as a coupling agent
IPC: Int.CL 7 C 07 K 1100
A ncw convcnicnt route for the sy nthesis of 3-amino mcthyl-3.5 .5 -trimcthy l-cyc lohexanol 5 and for two new intcrmedi atcs 1.3.3-trimcthy l-5-oxocyclohcxanc-carboxy lic acid a midc 3 and 5-hydroxy-1,3,3-trimethy l-cyc lohcxanc-carboxy li c ac id amide 4, has bccn reponed . Compound 5 has bccn identifi ed as an impon ant inhibitor o f influc nza viru s fu sion deri va ti ve and a pote nt and cffec ti vc surroga tc for thc quino li zidine mo icty .
v o
1
Synthcs is o f p-casomorph in H-Tyr-Pro- Phe- Pro-Gl yOH cmploy ing Boc-amino ac ids and Fmoc-C I as a coupling agent for pcptidc bond formation is descri bcd. The method is simple, c ffi cicnt and rapid .
Fmoc-CI, NMM Boc-Pro-OH + H-Gl y-OM e " )0 Boc-Pro-G ly-OMe ~ ~ ~ H-Tyr-Pro-Phe-Pro-G ly-OH
- IS C
v V Suresh Babu* & S J Tantry
A convenient synthesis of 1,2,4-triazolo[4,3-aJ[l,S]naphthyridines under solventless microwave irradiation
A simple and e ffi cie nt method for thc sy nthcsis of 4-aryl- I- (2- pyridy l)- I, 2, 4- tri azo lo[4, 3-a lll ,8 1-naphthyridines using iodobenzcnc di ace tatc (IBO) under mi crowave irradiati on is dcsc ribcd.
IPC: Int. C L7 C 07 0401100,249/24
Ph I (OAel, -. cxxAr
D ?" ~ ~
I I "'..-; ..-;
N N NHN= CH N MW
3 4
K Mogilaiah*, S Kavitha & G Ra ma Sudhakar
2619
INDIAN J C H EM, 43B (12) 2004
2620
2716
2719
2724
CONTENTS
Microwave-assisted rapid synthesis of thiosemicarbazide derivatives
IPC: Int.CI.7 C 07 C 337/06
R= a) 2-Pyridyl b) 3-Pyridyl c) 4-Pyridyl
Khosrow Zamani*, Khalil Faghihi, Shirindokht Bagheri & Mahdi Kalhor
+
Unusual migrations and cyclization in the preparation of J3-azido alcohols from J3-hydroxy esters
IPC: Int.CI? C 07 D 317/00
G Madhusudhan*, G Om Reddy, J Ramanatham & P K Dubey
Synthesis and antimicrobial screening of certain novel Mannich bases bearing 1,8-naphthyridine moiety
IPC: Int.CI.7 C 07 D 401/00 II A 61 P 31/04
K Mogilaiah* & B Sakram
..
Rapid and highly efficient synthesis of thiosemicarbazides by the coupling of isothiocyanate and carboxylic acid hydrazides in small amount of a polar solvent has been achieved under microwave irradiation by using a domestic microwave oven. The reaction proceeds rapidly, and is completed within 2-4 minutes giving a series of thiosemicarbazide derivatives 4-S(a-c) in high yields. All the compounds are fully characterized by Ff-IR, I H NMR, and mass spectroscopy.
W-NCS 3
t
MW. ~ U R-C-NHNHC-NHR'
4,5 (a-c)
R'= Benzyl and 2-methyl phenyl
Migration of TSDMS and Soc groups from 20
alcohols to 10 alcohols during the reduction of /3-hydroxy esters has been observed. Also. unusual cyclization has been noticed during tosylation of benzylic alcohol in tert-butyl«2R)-2-hydroxy-2-phenylethyl)carbonate with SN2 inversion.
H
% o~
'Cq)o o A series of novel Mannich bases 4 have bcen prepared from (2-oxo-3-phenyl-2H-[ I ,81naphthyridinI-yl)acetic acid hydrazide 1 and screened for their antibacterial activity.
~Ph
~.j( .. ,J" N7° nCR
CH2-CONHN I "Y ° N ~
I 1\ CH,-N X
- \~
4
INDIAN J CHEM, 43B (12) 2004
2727
2731
CONTENTS
Synthesis and antimicrobial screening of 2,4-diaryl-6-[2'H-[I']-4'-hydroxy-2'-oxo-benzopyran-3'-yl]pyridines and 2,6-diaryl-4-[2'H-[I']-4'hydroxy -2' -oxo-benzopyran-3' -y I]py ridines
IPC: Int.Ct.7 C 07 D 213/00 II A 61 P 31104
v V Mulwad* & D S Satwe
New biologically active constituents from Termillalia chebula stem bark
IPC: Int.Ct.7 A 61 K 35/78 II C 07 D 311132
A facile synthesis of 2,4-diaryl-6-[2'H-[I']-4'hydroxy-2' -oxo-benzopyran-3' -y l]pyridine and 2,6-diaryl-4-[2' H-[ I ']-4' -hydroxy-2' -oxo-benzopyran-3'yl]pyridines.
4/1
Evidences are presented for the isolation and structures of two new compounds namely, 5,7, 2'-triO-methylnavanone-4'-O-~- D-galactopyranosyl-( I ~ 3)-~-D-glucopyranoside 1 and 2ex, 19ex-dihydroxy-3-oxo- 12-en-28-oic acid-28-oic acid-O- ex -L-rhamnopyranosyl-(J ~ 4)-~-D-glucopyranoside 2 from the bark of Terminalia chebula which are obtained along with known substances ~-amyrin, lupeol and friedelin . Compound 1 displays antifungal activity while compound 2 exhibits both antifungal and antifeedant activities.
8 9 0
, 3
2 1J \\ '~' OH \ 4 6 II
- , 0 " 5" 4 5 0 OH
1" HO ,, 0 3
OH
1
29 30 HO
25
HO,,2 8 15
3 27
22 l' 5 OH
COO/\-O~ 16 28 ur.~O
HO, OH .' 2
5
4 7 0 5
6
OH
23 24 2 OH
S K Srivastava* & S D Srivastava
2621
INDIAN J CHEM, 43B (12) 2004
2622 CONTENTS
2734 A new sesquiterpcne lac tone from Artemisia A new rearranged farnesy loxy sesquiterpene lactone 1 0/1/1110 leaves has been isolated from the leaves of /\rtelllesia
alln/la . The structure of th is compound has been IPC: InLCI .7 C 07 A 61 K 31/00 established as 5a-13' ( IY),7' (14') , 11' ( 13')-t rien] pen
tadccenyloxydihydrortean nuin. 8(1) on the basis of its spectral analys is.
\0 """ .... ' ...... ,
"
"'O~ryvy
Tarun Singh & R S Bhakuni*
Authors for correspondence arc indi cated by (*)
IPC : Internationa l Patent Class ification Int. CI.: Internationa l Classification 7 ed ition, 1999
INDI AN J C HEM, 43B ( 12) 200~
Recommended