Synthesis 2012; 44(19): 3085-3089
DOI: 10.1055/s-0032-1317034
paper
© Georg Thieme Verlag Stuttgart · New York

New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis–Hillman Adducts

Ying Zhong
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   Email: mwding@mail.ccnu.edu.cn
,
Lei Wu
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   Email: mwding@mail.ccnu.edu.cn
,
Ming-Wu Ding*
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   Email: mwding@mail.ccnu.edu.cn
› Author Affiliations
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Publication History

Received: 08 May 2012

Accepted after revision: 16 July 2012

Publication Date:
08 August 2012 (online)


Abstract

Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.

Supporting Information