An efficient and novel strategy has been developed using liquid liquid phase transfer catalysis conditions for the synthesis of 2-amino-4,6-diarylnicotinonitrile and 5,7-diaryltetrazolo[1,5-a]pyridine-8-carbonitrile. The former was obtained either by two step process involving azidolysis of 2-chloro-4,6-diarylnicotinonitrile followed by chemoselective reduction of tetrazole moiety while facile one-pot procedure was conveniently carried out from corresponding 2-chloro-4,6-diarylnicotinonitrile.

1 was reacted with ethyl 2-mercaptoacetate 2 to furnish ethyl 2-(3-cyano-4,6-diarylpyridin-2-ylthio)acetate 3 as intermediates. These intermediates were cyclized by Thorpe-Zeigler cyclization using solid-liquid phase-transfer catalysis conditions to give ethyl 3-amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxylate 4. One-pot heterocyclization without isolating the intermediates was also achieved using solid-liquid phase transfer conditions.

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Simultaneous C-and N-Alkylation of 2-Oxo-4,6-diaryl-1,2,3,4-tetrahydropyridine-3-carbonitrile under Solid-Liquid Phase-Transfer Conditions. -Unprecedented simultaneous C-and N-alkylation of pyridine-3-carbonitriles (I) is achieved under solid-liquid phase-transfer conditions. Tandem hydrolysis-decarboxylation of the reaction products (III) (9 examples) provides 1,3-dialkylpyridinone derivatives (IV) (yields not given). -(SHAH, H. C.; SHAH, V. H.; DESAI*, N. D.; Synth. Commun.

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