Efficient Iminophosphorane‐Mediated Preparation of Benzofuro[3,2‐d]pyrimidin‐4(3H)‐ones and Unexpected Ring Opening Products |
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Authors: | Yang‐Gen Hu Ming‐Guo Liu Ming‐Wu Ding |
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Affiliation: | 1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P.?R. China (fax +86‐27‐67862041);2. Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, P.?R. China |
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Abstract: | The carbodiimides 4 , obtained from aza‐Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines, phenols or alcohols in the presence of catalytic amounts of K2CO3 or sodium alkoxide to give 2‐substituted benzofuro[3,2‐d]pyrimidin‐4(3H)‐ones 6 . However, when 2,2′‐iminobis[ethanol] was used, the unexpected ring opening product 7 was formed instead of 6 . Reaction of 4 with primary amines RNH2 (R=Et, Pr, Bu, etc.) gave guanidine intermediates 8 , which were further treated with EtONa to give only one regioisomer 9 via a base catalyzed cyclization. However, another regioisomer 11 was obtained when NH3 or ‘small’ amines RNH2 (R=Me, NH2) were used in the absence of EtONa via a spontaneous cyclization of 8 . |
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Keywords: | Benzofuro[3,2‐d]pyrimidin‐4(3H)‐ones Iminophosphoranes Carbodiimides Aza‐Wittig reaction |
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