61
Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides. Goverdhan Surineni a , Perumal Yogeeswari b and Dharmarajan Sriram b , Srinivas Kantevari a,c a Organic Chemistry Division-II (CPC Division), CSIR- Indian Institute of Chemical Technology, Hyderabad- 500 007, Telangana, INDIA. b Medicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad-500078, Telangana, INDIA. c Academy of Scientific and innovative Research, CSIR- Indian Institute of Chemical Technology, Hyderabad-500 007, Telangana, INDIA. Supporting Information Table of Contents ---------------------------------------------------------------- Page 1. General Experimental procedures and spectral data: S2 2. 1H NMR, 13C NMR and HRMS spectra of 2, 3, 4 and 6a-p: S3-S59 Corresponding author. Tel.: +91-4027191437; fax: +91-4027198933; e-mail: [email protected] , [email protected] . 1

ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

  • Upload
    others

  • View
    1

  • Download
    0

Embed Size (px)

Citation preview

Page 1: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

Click-based synthesis and antitubercular evaluation of dibenzofuran tethered thiazolyl-1,2,3-triazolyl acetamides.

Goverdhan Surinenia, Perumal Yogeeswarib and Dharmarajan Sriramb, Srinivas Kantevaria,c

a Organic Chemistry Division-II (CPC Division), CSIR- Indian Institute of Chemical Technology, Hyderabad-500

007, Telangana, INDIA. bMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology

& Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad-500078, Telangana, INDIA.cAcademy of Scientific and innovative Research, CSIR- Indian Institute of Chemical Technology, Hyderabad-500

007, Telangana, INDIA.

Supporting Information

Table of Contents ---------------------------------------------------------------- Page

1. General Experimental procedures and spectral data: S2

2. 1H NMR, 13C NMR and HRMS spectra of 2, 3, 4 and 6a-p: S3-S59

Experimental Section:

Corresponding author. Tel.: +91-4027191437; fax: +91-4027198933; e-mail: [email protected], [email protected].

1

Page 2: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

All the reactions were monitored by TLC (Precoated silica plates and visualizing under UVlight).

Air-sensitive reagents were transferred by syringe or double-ended needle. Evaporation of

solvents was performed at reduced pressure on a Buchi rotary evaporator.1H and 13C NMR

spectra of samples in CDCl3 and DMSO-d6 were recorded on Bruker UXNMR FT-300MHz

(Avance) spectrometer and Varian FT-500MHz (Inova). Chemical shift reported are relative to

an internal standard TMS (δ=0.0). Mass spectra were recorded in ESI conditions at 70 eV on an

LC-MSD (Agilent technologies) spectrometers. All high-resolution spectra were recorded on

QSTAR XL hybrid MS/MS system (Applied Bio systems/ MDS sciex, foster city, USA),

equipped with an ESI source (IICT, Hyderabad). Column chromatography was performed on

silica gel (60-120 mesh) supplied by Acme Chemical Co., India. TLC was performed on Merck

60 F-254 silica gel plates. Commercially available anhydrous solvents CH2Cl2, DMF, MeOH,

Acetone, t-BuOH and EtOAc were used as such without further purification.

2

Page 3: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

3

Page 4: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

4

Page 5: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

5

Page 6: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

6

Page 7: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

7

Page 8: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

8

Page 9: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

9

Page 10: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

10

Page 11: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

11

Page 12: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

12

Page 13: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

13

Page 14: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

14

Page 15: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

15

Page 16: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

16

Page 17: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

17

Page 18: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

18

Page 19: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

19

Page 20: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

20

Page 21: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

21

Page 22: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

22

Page 23: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

23

Page 24: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

24

Page 25: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

25

Page 26: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

26

Page 27: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

27

Page 28: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

28

Page 29: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

29

Page 30: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

30

Page 31: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

31

Page 32: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

32

Page 33: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

33

Page 34: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

34

Page 35: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

35

Page 36: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

36

Page 37: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

37

Page 38: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

38

Page 39: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

39

Page 40: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

40

Page 41: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

41

Page 42: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

42

Page 43: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

43

Page 44: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

44

Page 45: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

45

Page 46: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

46

Page 47: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

47

Page 48: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

48

Page 49: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

49

Page 50: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

50

Page 51: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

51

Page 52: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

52

Page 53: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

53

Page 54: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

54

Page 55: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

55

Page 56: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

56

Page 57: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

57

Page 58: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

58

Page 59: ars.els-cdn.com€¦ · Web viewbMedicinal Chemistry and Antimycobacterial Research Laboratory, Pharmacy Group, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar

59