One-pot and regioselective synthesis of polysubstituted 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by sequential Ugi/Staudinger/aza-Wittig reaction |
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| Authors: | Jun Xiong Xiao Wei Yu-Chen Wan Ming-Wu Ding |
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| Affiliation: | 1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, PR China;2. College of Pharmacy, Hubei University of Science and Technology, Xianning, Hubei, 437100, PR China |
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| Abstract: | An efficient one-pot and regioselective synthesis of 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi reactions of 2-azidobenzylamines, aldehydes, acids (or α-keto acids) and isocyanides produced the azide intermediates, which were then treated with tributylphosphine or triphenylphosphine to give polysubstituted 3,4-dihydroquinazolines or 4,5-dihydro-3H-1,4-benzodiazepin-3-ones in moderate to good yields by tandem Standinger/aza-Wittig reactions. |
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| Keywords: | 3,4-Dihydroquinazoline Ugi reaction Standinger reaction Aza-Wittig reaction |
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