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Studies on isocyanides and related compounds. – Synthesis and cyclization ofN-substituted 1-isocyano-1-cycloalkanecarboxamides

✍ Scribed by Bossio, Ricardo ;Marcaccini, Stefano ;Paoli, Paola ;Papaleo, Sandro ;Pepino, Roberto ;Polo, Cecilia

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
481 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The Ugi four‐component condensation between cycloalkanones, isocyanides, and ammonium formate affords N‐substituted 1‐formylamino‐1‐cycloalkanecarboxamides 1 which are dehydrated to give the corresponding isocyanides 2. Compounds 2 are cyclized with arylsulfenyl thiocyanates to 1,3‐diazaspiro‐2‐thiones 4 and 5. A series of 1,3‐diazaspiro[4,5]dec‐1‐en‐4‐ones 7 is prepared by cyclizing 2c–j with butyllithium. The structures of these compounds are confirmed by means of IR, ^1^H‐NMR, and X‐ray analysis.

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