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New efficient synthesis of 1,2,4-trisubstituted imidazoles and imidazo[1,2- c]quinazolines by a tandem aza-Wittig/electrocyclic ring-closure process

A series of 1,2,4-trisubstituted imidazoles 5 were synthesized efficiently by a tandem aza-Wittig/1,5-electrocyclic ring-closure reaction of vinyliminophosphoranes 3 with aldehydes. Reactions of 5s, t with triphenylphosphine produced iminophosphoranes 7. A tandem aza-Wittig reaction of iminophosphor...

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Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (4), p.965-971
Main Authors: Nie, Yi-Bo, Duan, Zhuan, Ding, Ming-Wu
Format: Article
Language:English
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Summary:A series of 1,2,4-trisubstituted imidazoles 5 were synthesized efficiently by a tandem aza-Wittig/1,5-electrocyclic ring-closure reaction of vinyliminophosphoranes 3 with aldehydes. Reactions of 5s, t with triphenylphosphine produced iminophosphoranes 7. A tandem aza-Wittig reaction of iminophosphorane 7 with isocyanate generated imidazo[1,2-c]quinazolines 9 in high yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.12.005