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Studies on isocyanides and related compounds. – Synthesis and cyclization of N ‐substituted 1‐isocyano‐1‐cycloalkanecarboxamides
Author(s) -
Bossio Ricardo,
Marcaccini Stefano,
Paoli Paola,
Papaleo Sandro,
Pepino Roberto,
Polo Cecilia
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101145
Subject(s) - chemistry , condensation , ammonium , ammonium formate , butyllithium , isocyanide , medicinal chemistry , organic chemistry , acetonitrile , physics , thermodynamics
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.