Efficient Synthesis of Tetrahydrobenzo[b]pyrans under Solvent‐Free Conditions at Room Temperature

Liangce Rong Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China; Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, ChinaCorrespondence[email protected]

Xiaoyue Li Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China

Haiying Wang Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China

Daqing Shi Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China; Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, China

Shujiang Tu Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China; Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, China

Qiya Zhuang Department of Chemistry, Xuzhou Nornal University, Xuzhou, Jiangsu, China; Key Laboratory of Biotechnology on Medical Plant, Xuzhou, Jiangsu, China

Pages 2363-2369 | Published online: 22 Sep 2006

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https://doi.org/10.1080/00397910600640230

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Abstract

A range of tetrahydrobenzo[b]pyrans have been synthesized in very good yields under solvent‐free conditions by grinding α‐cyanocinnamonitrils or β‐cyano‐β‐carbethoxy styrene and 5,5‐dimethyl‐1,3‐cyclohexanedione in the presence of TEBA as catalyst. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive.

Keywords:

α‐Cyanocinnamonitrils
β‐cyano‐β‐carbethoxy styrene
solvent‐free conditions
tetrahydrobenzo[b]pyrans

Acknowledgment

We are grateful to Natural Science Foundation (04XLB14) of Xuzhou Normal University and the Foundation of the Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province for financial support.

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