Journal
TETRAHEDRON
Volume 68, Issue 27-28, Pages 5612-5618Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.065
Keywords
o-Quinone methides; 2-Amino-4H-chromene-2-carbonitriles; 5H-Chromeno[2,3-b]pyridine-3-carbonitriles; Synthesis in water; 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)
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Funding
- program of the President of the Russian Federation for state support of young Russian scientists - Candidates of sciences [MK-3368.2011.3]
- Russian Ministry of Education and Science
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We have reported DBU catalyzed synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles in water under reflux. The attractive features of this process are mild reaction conditions, short reaction times, easy isolation of products and good yields. 5H-chromeno[2,3-b]pyridine-3-carbonitriles were obtained by refluxing excess of malononitrile and quaternary ammonium salts in ethanol in the presence of NaOH as catalyst. The mechanisms of these reactions are believed to involve the formation of the o-quinone methide intermediate. (c) 2012 Elsevier Ltd. All rights reserved.
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