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Paper | Regular issue | Vol 75, No. 9, 2008, pp.2251-2261
Published online, 12th May, 2008
DOI: 10.3987/COM-08-11390
The Synthesis and Microbiological Activity of 2-Mercapto-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile Derivatives

Agnieszka Miszke,* Henryk Foks, Anna Kedzia, Ewa Kwapisz, and Zofia Zwolska

*Department of Organic Chemistry, Medical University of Gdansk, Poland

Abstract

Synthesis of 2-mercapto-4-(pyrrolidin-1-yl)pyridine derivatives starting from 2-bromo-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile (1) is described. The desired derivatives of 2-(phenylthio)-4-(pyrrolidin-1-yl)pyridine- 3-carbonitrile were obtained in reaction of 1 with suitable thiophenoles, while reaction with benzyl mercaptan gave a related thiobenzyl derivative. Alternatively, compound 1 was transformed into 2-mercapto-4-(pyrrolidin-1-yl)pyridine- 3-carbonitrile (2). Reaction of 2 with chloroacetic acid or chloroacetone derivatives gave related products of mercapto group substitution. The latter compounds could be cyclized in Thorpe-Ziegler reaction to related 3-amino-4- (pyrrolidin-1-yl)thieno[2,3-b]pyridine derivatives. Reaction of 2 with sodium hydroxylamino-O-sulphonate gave the related aminosulfanyl derivative. Selected product were screened for bacteriostatic and antituberculosis activity, and some of them exhibited a significant activity.