

SYNTHESIS OF 2-(1-ARYL-1H-TETRAZOL-5-YL)-THIENO[2,3-b]PYRIDINE DERIVATIVES

Abstract
Alkylation of 4,6-dimethyl-2-sulfanylpyridine-3-carbonitrile with 1-aryl-5-(chloromethyl)-1H-tetrazoles yielded 2-{[(1-aryl-1H-tetrazol-5-yl)methyl]sulfanyl}-4,6-dimethylpyridine-3-carbonitriles, which easily cyclize by the action of bases to form 2-(1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives. The use of excess base in the alkylation step leads to direct formation of cyclized products in high yields.
Keywords
1-aryl-(5-chloromethyl)-1H-tetrazole; 2-{[(1H-tetrazol-5-yl)methyl]sulfanyl}pyridine; 2-(1H-tetrazol-5-yl)thieno[2,3-b]- pyridine; alkylation; bioisostere; heterocyclization.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv