Heterocycles p. 1055 - 1066 (1993)
Update date:2022-07-30
Topics:
Wamhoff, Heinrich
Schmidt, Andreas
Recent examples of the three component reaction: iminophosphoranes / isocyanates / heteroarenes (imines) are described.The uracil (1) affords with O-methyl-ε-caprolactim ether and isocyanates the pyrimido<4',5':4,5>pyrimido<6,1-a>azepines (6a-c) and with benzylideneaniline (8) the pyrimido<4,5-d>pyrimidines (9a-d), while azodicarboxylate gives the isofervenuline, pyrimido<4,5-e><1,2,4>triazine (11).Furthermore, pyrimido<4,5-d>pyrimidine (15) is obtained via 14 from 1, N-phenylbenzimidoyl chloride (13), and phenylisocyanate, while the tautomeric mixture 17A <=> 17B results from treatment of 6-aminouracil (16) with 13; interception with dimethyl acetylenedicarboxylate gives the pyrido<2,3-d>pyrimidine (19).
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