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. 2022 Oct 18;12(46):29840-29843.
doi: 10.1039/d2ra04936h. eCollection 2022 Oct 17.

Condensation of acrylonitrile and aryl acetonitrile: construction of α-amino-β-cyano cyclohexene skeletons

Wei Zhang  1 , Chuan-Su Tang  2 , Shi-Qun Xiang  3   4
Affiliations

Condensation of acrylonitrile and aryl acetonitrile: construction of α-amino-β-cyano cyclohexene skeletons

Wei Zhang et al. RSC Adv. .

Abstract

A representative condensation of acrylonitrile and aryl acetonitrile has been reported for the synthesis of α-amino-β-cyano cyclohexene. The reaction was carried out mildly in an open environment at room temperature. The scope and versatility of the method have been demonstrated with 20 examples, containing highly active ethynyl groups. Further applications for 4-aminopyrimidine compounds were performed. A mechanism was proposed, involving Michael additions between acrylonitrile and aryl acetonitriles as well as intramolecular condensation.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Selected examples and previous works.
Scheme 1
Scheme 1. Mechanistic studies and gram-scale experiments.
Scheme 2
Scheme 2. Applications of the products.
Fig. 2
Fig. 2. Crystal structures of compounds 3a (CCDC 2158344) and 5a (CCDC 2158132).
Scheme 3
Scheme 3. Possible reaction mechanism.
See this image and copyright information in PMC

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