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Reactions of carbonyl diisocyanate with amides and acids
Author(s) -
Akteries Bernhard,
Jochims Johannes C.
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190226
Subject(s) - chemistry , nucleophile , halide , urea , primary (astronomy) , organic chemistry , acetylation , polymer chemistry , medicinal chemistry , catalysis , biochemistry , physics , astronomy , gene
Carbonyl diisocyanate ( 1 ) reacts with primary amides to give 1‐acylated isocyanuric acids ( 5,6 ). With secondary amides, 1 affords the rather instable oxadiazinediones 4 , which for certain substituents rearrange to give triazines ( 5,10 ). With nucleophiles, compounds 4 give oligourets, e.g. with ureas pentaurets ( 11,12 ) were obtained. Carbonyl diisocyanate reacts with hydrogen halides to afford the crystalline urea‐1,3‐dicarbonyl halides 13a – c . Diverse products ( 16,17,24,26 ) were obtained with carboxylic acids. In most cases oxadiazinediones ( 26 ) were isolated, which can be transformed with nucleophiles into acyl ureas 30,31 , biurets 32 , and triurets 33 . Acetylation of 26 leads to the reactive heterocycles 34 .