Rapid Access for the Synthesis of 1‐N‐Methyl‐spiro[2.3′]oxindole‐spiro[3.7″] (3″‐Aryl)‐5″‐methyl‐3″,3a″,4″,5″,6″,7″‐hexahydro‐2H‐pyrazolo[4,3‐ c ]pyridine‐4‐aryl‐pyrrolidines Through Sequential 1,3‐Dipolar Cycloaddition and Annulation

Author: Sridhar Gowri   Raghunathan R.  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.36, Iss.1, 2006-02, pp. : 21-29

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Abstract

The 1,3-dipolar cycloaddition of an azomethine ylide, generated from isatin and sarcosine by a decarboxylative route with various p -substituted 3,5 bis(aryl methylidene)N-methyl-4-piperidinones in refluxing methanol, proceeded regioselectively to give novel dispiroheterocycles. The product on subsequent annulation with hydrazine hydrate afforded 1-N-methyl-spiro[2.3']oxindole-spiro[3.7?](3?-aryl)-5?-methyl-3?,3a?,4?,5?,6?,7?-hexahydro-2H-pyrazolo[4,3- c ]pyridine-4-aryl-pyrrolidines in good yield.

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