Synthesis 2012; 44(10): 1559-1568
DOI: 10.1055/s-0031-1290976
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene Catalyzed Intramolecular Hydroacylation of Alkynylphosphonates

Zhenqiang Wang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   eMail: chshidq@mail.ccnu.edu.cn
,
Zhihua Yu
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   eMail: chshidq@mail.ccnu.edu.cn
,
Ying Wang
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   eMail: chshidq@mail.ccnu.edu.cn
,
Deqing Shi*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041   eMail: chshidq@mail.ccnu.edu.cn
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Publikationsverlauf

Received: 13. Januar 2012

Accepted after revision: 24. März 2012

Publikationsdatum:
02. Mai 2012 (online)


Abstract

Two exocyclic and endocyclic olefin tautomers of chromone phosphonates were obtained in good to excellent yields at different temperatures by utilizing an N-heterocyclic carbene catalyst in the intramolecular reactions between the formyl group and alkynylphosphonates. The exocyclic olefins can isomerize to the endocyclic derivatives completely when treated with a thiazolium salt precatalyst and potassium carbonate at 30 °C for three to five hours. In addition, the chromone phosphonate derivatives were also applied in the one-pot synthesis of benzopyranopyridine phosphonates in moderated yields.

 
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