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Open AccessArticle

K2CO3-Mediated Synthesis of Functionalised 4-Substituted-2-amino-3-cyano-4H-chromenes via Michael-Cyclization Reactions

by Yanyang He 1,†, Rong Hu 1,†, Rongsheng Tong 2, Fengqiong Li 1, Jianyou Shi 2,* and Mei Zhang 1,*
1
Key Laboratory of Standardization of Chinese Herbal Medicines of Ministry of Education, State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
2
Pharmaceutical Department of Sichuan Academy of Medical Sciences, Sichuan Provincial People's Hospital, Chengdu 610072, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2014, 19(12), 19253-19268; https://doi.org/10.3390/molecules191219253
Received: 14 September 2014 / Revised: 23 October 2014 / Accepted: 5 November 2014 / Published: 25 November 2014
(This article belongs to the Section Organic Chemistry)
An efficient approach for the synthesis of functionalized 4-substituted-2-amino-3-cyano-4H-chromenes moderate to high yields (up to 98%) has been achieved via a tandem K2CO3 catalyzed conjugate addition-cyclization reaction of malononitrile and a range of Knoevenagel adducts previously formed from oxindole, pyrazolone, nitromethane, N,N-dimethylbarbituric acid or indanedione. This methodology differs from the previous classical methods in its simplicity and ready availability of the catalyst. View Full-Text
Keywords: 2-amino-4H-chromenes; Michael-cyclization; malononitrile; K2CO3; Knoevenagel adducts; cascade reaction 2-amino-4H-chromenes; Michael-cyclization; malononitrile; K2CO3; Knoevenagel adducts; cascade reaction
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He, Y.; Hu, R.; Tong, R.; Li, F.; Shi, J.; Zhang, M. K2CO3-Mediated Synthesis of Functionalised 4-Substituted-2-amino-3-cyano-4H-chromenes via Michael-Cyclization Reactions. Molecules 2014, 19, 19253-19268.

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