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Communication | Special issue | Vol 82, No. 1, 2010, pp.305-311
Published online, 27th July, 2010
DOI: 10.3987/COM-10-S(E)66
Synthesis of 2,3,4-Tri-Substituted 3,4-Dihydroquinazolines via Tandem Nucleophilic Addition/Epoxy Ring-Opening Cyclization Methodology Using N-(2-Oxiranylphenyl)carbodiimides with Nucleophiles

Takao Saito,* Tatsuya Ote, Masahiro Shiotani, Hiroko Kataoka, Takashi Otani, and Noriki Kutsumura

*Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


N-(2-Oxiranylphenyl)carbodiimides, which were synthesized via an aza-Wittig reaction of the corresponding functionalized iminophosphoranes with aromatic and aliphatic isocyanates, underwent O-, S-, C-, or N-nucleophilic addition onto a cumulene, followed by an epoxy ring-opening cyclization with the newly formed NH-nucleophile in a one-pot reaction to furnish 2,3-disubstituted 4-(hydroxymethyl)-3,4-dihydroquinazolines in a highly stereospecific manner.