e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Benzotriazole-assisted thioacylation

…, V Rodriguez-Garcia, PP Mohapatra…

Index: Katritzky, Alan R.; Witek, Rachel M.; Rodriguez-Garcia, Valerie; Mohapatra, Prabhu P.; Rogers, James W.; Cusido, Janet; Abdel-Fattah, Ashraf A. A.; Steel, Peter J. Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 7866 - 7881

Full Text: HTML

Citation Number: 44

Abstract

Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/ alkoxythioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.

4-Nitrobenzoyl chloride Structure

4-Nitrobenzoyl ...

1,2-Diamino-4-nitrobenzene Structure

1,2-Diamino-4-n...

~84%

N-(2-amino-5-nitrophenyl)-4-nitrobenzamide Structure

N-(2-amino-5-ni...

(4-bromophenyl)(6-nitrobenzotriazol-1-yl)methanethione Structure

(4-bromophenyl)...

morpholine Structure

~90%

(4-bromophenyl)-morpholin-4-ylmethanethione Structure

(4-bromophenyl)...

N-(2-amino-5-nitrophenyl)-4-bromobenzylamide Structure

N-(2-amino-5-ni...

~%

(4-bromophenyl)-morpholin-4-ylmethanethione Structure

(4-bromophenyl)...

N/A Structure

~%

(4-bromophenyl)-morpholin-4-ylmethanethione Structure

(4-bromophenyl)...

4-Bromobenzoyl chloride Structure

4-Bromobenzoyl ...

~%

(4-bromophenyl)-morpholin-4-ylmethanethione Structure

(4-bromophenyl)...

Bis(1-benzotriazolyl)methanethione Structure

Bis(1-benzotria...

Benzocaine Structure

~99%

Benzoic acid,4-isothiocyanato-, ethyl ester Structure

Benzoic acid,4-...

(1H-benzo[d][1,2,3]triazol-1-yl)(p-tolyl)methanethione Structure

(1H-benzo[d][1,...

Benzylamine Structure

~96%

N-benzyl-4-methylbenzenecarbothioamide Structure

N-benzyl-4-meth...

P-TOLYLMAGNESIUM BROMIDE Structure

P-TOLYLMAGNESIU...

~%

N-benzyl-4-methylbenzenecarbothioamide Structure

N-benzyl-4-meth...

Propanoyl chloride Structure

Propanoyl chloride

1,2-Diamino-4-nitrobenzene Structure

1,2-Diamino-4-n...

~82%

N-(2-amino-5-nitrophenyl)propanamide Structure

N-(2-amino-5-ni...

(1H-benzo[d][1,2,3]triazol-1-yl)(4-methoxyphenyl)methanethione Structure

(1H-benzo[d][1,...

Piperidine Structure

~95%

(4-methoxyphenyl)-piperidin-1-ylmethanethione Structure

(4-methoxypheny...

4-Anisylmagnesium bromide Structure

4-Anisylmagnesi...

~%

(4-methoxyphenyl)-piperidin-1-ylmethanethione Structure

(4-methoxypheny...

2-Aminopyridine Structure

2-Aminopyridine

Bis(1-benzotriazolyl)methanethione Structure

Bis(1-benzotria...

~82%

Thiourea,N,N'-di-2-pyridinyl- Structure

Thiourea,N,N'-d...

(benzotriazol-1-yl)phenylmethanethione Structure

(benzotriazol-1...

Benzylamine Structure

~96%

Benzenecarbothioamide,N-(phenylmethyl)- Structure

Benzenecarbothi...