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Title: An efficient synthesis of chromene derivatives through a tandem michael addition-cyclization reaction
Authors: Jaman, Zinia
Jahan, Khorshada
Akhter, Kawsari
Romman, U. K. R.
Ahmed, S. Mosaddeq
Siddiki, S. M. A. Hakim
Ahmed, M. Giasuddin
Keywords: Tandem Michael addition, chromene derivatives, 1,3-cyclohexanedione
Issue Date: Jan-2013
Publisher: Bangladesh Chemical Society (BCS)
Series/Report no.: 26(1);Page 75-82
Abstract: The racemic synthesis of ethyl esters of 2-amino-5-oxo-4-aryl-5, 6, 7, 8-tetrahydro-4H-chromene-3-carboxylic acid 3a-d was achieved through a tandem Michael addition-cyclization reaction of easily available cyclohexane-1,3-dione 2a, 5, 5-dimethyl-1,3-cyclohexanedione 2b and ethyl esters of 2-cyano-3-arylacrylic acid 1a-d. The reaction of 1b with 2a yielded 2,5-dioxo-4-phenyl-3,4,5,6,7,8-hexahydro- 2H-chromene-3-carbonitrile 4e resulting from a different mode of cyclization. High addition-cyclization efficiency was observed with good yields (up to 93%) using alcoholic sodium ethoxide as a base catalyst, which provides a competitive method for the synthesis of chromene derivatives under a simple efficient way.
ISSN: 1022-016X
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