New synthetic approaches to condensed and spiro coumarins: Coumarin-3-thiocarboxamide as building block for the synthesis of condensed and spiro coumarins

Article abstract of DOI:10.1080/10426500008043675

Coumarin-3-thiocarboxamide 1 was reacted with malononitrile, cyanoacetamide or cyanothioacetamide to give the corresponding thiopyrano(3,4-c)coumarin-1-carbonitrile 2. Also, compound 1 was reacted with a variety of active methylenes having an α-cyano or α-keto group to give thiopyranocoumarin derivatives 3-9. The reaction of compound 1 with different ketene N.S-acetals, afforded the corresponding thiazino(5,4-c)coumarin derivatives 10,13 and 16. On reacting compound 10 or 13 with malononitrile, spiro pyran-4,2′-thiazino(5,4-c)coumarin 11 or 14 were obtained, while the reaction of compound 16 with malononitrile gave spiro cyclobutene-1,2′-thiazino(5,4-c)coumarin derivative 17. Treating of compounds 10, 13 or 16 with cyclohexylidenemalomonitrile afforded spiro naphthyl-1,2′-thiazino(5,4-c) coumarin derivatives 12,15 or 18 respectively. Treatment of compound 1 with CS₂and malononitrile under PTC condition afforded 1,3-dithiano(5,4-c) coumarin derivative 19, which in turn reacted with malononitrile or cyclohexylidenemalononitrile to afford spiro cyclobut-2-enyl-1,2′-(1,3)dithiano(5,4-c)coumarin 20 and spiro naphthyl-1,′2-(1,3)dithiano(5,4-c)coumarin 21 derivatives, respectively.

Full text of DOI:10.1080/10426500008043675

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Phosphorus, Sulfur, and Silicon
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NEW SYNTHETIC APPROACHES
TO CONDENSED AND SPIRO
COUMARINS: COUMARIN-3-
THIOCARBOXAMIDE AS
BUILDING BLOCK FOR THE
SYNTHESIS OF CONDENSED AND
SPIRO COUMARINS
A. M.M. El-Saghier a & A. Khodairy a
a Chemistry Department, Faculty of Science, Sohag,
Egypt
Version of record first published: 04 Oct 2006
To cite this article: A. M.M. El-Saghier & A. Khodairy (2000): NEW SYNTHETIC
APPROACHES TO CONDENSED AND SPIRO COUMARINS: COUMARIN-3-THIOCARBOXAMIDE
AS BUILDING BLOCK FOR THE SYNTHESIS OF CONDENSED AND SPIRO COUMARINS,
Phosphorus, Sulfur, and Silicon and the Related Elements, 160:1, 105-119
To link to this article: http://dx.doi.org/10.1080/10426500008043675
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