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Studies on isocyanides and related compounds. An unusual synthesis of imidazolyloxazolones

✍ Scribed by Ricardo Bossio; Stefano Marcaccini; Roberto Pepino; Paola Paoli

Book ID
112130942
Publisher
Journal of Heterocyclic Chemistry
Year
1994
Tongue
English
Weight
229 KB
Volume
31
Category
Article
ISSN
0022-152X

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ChemInform Abstract: Studies on Isocyani
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Studies on Isocyanides and Related Compounds. An Unusual Synthesis of Functionalized Succinimides. -The reaction of amides (V) affords succinimides such as (VI) instead of the expected β-lactam. A possible reaction mechanism is described.

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## Abstract The reaction between arylglyoxals (1), cyclohexyl isocyanide, and aromatic carboxylic acids (2) affords __N__‐cyclohexyl‐2‐acyloxy‐3‐aryl‐3‐oxopropionic amides (3) which can be cyclized to __N__‐cyclohexyl‐2,4‐diaryl‐5‐oxazolecarboxamides (4).

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## Abstract The Ugi four‐component condensation between 1,1‐diethoxy‐2‐isocyanoethane (2), cycloketones 1, amine hydrochlorides 4, and potassium thiocyanate (3a) or selenocyanate (3b) affords spiroimidazoles 5, which are cyclized to spiroimidazo[1,5‐__a__]imidazole‐5‐thiones (or selenones) 6.

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## 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‐