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Using Morita–Baylis–Hillman acetates of 2-azidobenzaldehydes for the synthesis of 2-alkoxy-3-cyanomethylquinolines and alkyl quinoline-3-carboxylates

✍ Scribed by Hea Jung Kim; Eun Mi Jeong; Kee-Jung Lee

Book ID
102344195
Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
135 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A simple method for the synthesis of several 2‐alkoxy‐3‐cyanomethylquinolines and alkyl quinoline‐3‐carboxylates using iminophosphorane‐mediated cyclization reactions of 3‐(2‐azidophenyl)‐2‐cyanomethylpropenoates and 3‐(2‐azidophenyl)‐2‐nitromethylpropenoates has been developed. These compounds were readily obtained from the Morita–Baylis–Hillman acetates of 2‐azidobenzaldehydes using potassium cyanide or sodium nitrite, respectively. J. Heterocyclic Chem., (2011)

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Synthesis of ethyl 3-cyano-2-methylcinna
Synthesis of ethyl 3-cyano-2-methylcinnamates and 3-cyano-2-methylcinnamonitriles from the Baylis–Hillman acetates
✍ Yun Mi Chung; Ji Hyeon Gong; Taek Hyeon Kim; Jae Nyoung Kim 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 68 KB

The reaction of the DABCO salts 2, generated in situ from the Baylis-Hillman acetates 1, and KCN in aqueous THF gave ethyl 3-cyano-2-methylcinnamates 4a-d and 3-cyano-2-methylcinnamonitriles 4e-f in good yields.