Reactions of some N-( 2,5-dimethoxyaryl)thiobenzamides: en route to an analogue of kuanoniamine A

Citation
Ya. Jackson et al., Reactions of some N-( 2,5-dimethoxyaryl)thiobenzamides: en route to an analogue of kuanoniamine A, J CHEM S P1, (2), 2000, pp. 205-210
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
2
Year of publication
2000
Pages
205 - 210
Database
ISI
SICI code
0300-922X(2000):2<205:ROSN2E>2.0.ZU;2-X
Abstract
Nitration of 2-aryl-4,7-dimethoxybenzothiazoles 7a-7c produces a mixture of 5- and 6-nitrobenzothiazoles which were distinguished by synthesis of the 2-aryl-4,7-dimethoxy-6-nitrobenzothiaoles 12a-12c by oxidative cyclization of the corresponding nitrothiobenzanilides. Reaction of N-[2,5-dimethoxy-4- (p-tolylsulfonylamino)phenyl]thiobenzamide 17d with base to give 5-methoxy- 2-phenyl-6-(p-tolylsulfonylamino)benzothiazole 18 with apparent intramolecu lar replacement of a methoxy group is also described.