Synthesis of Novel 1,2,3,4-Tetrahydrocarbazole Derivatives of Biological Interest

2-Cyano-N-(tetrahydrocarbazole)acetamide (1) was utilized for the synthesis of several new arylazocarbazole derivatives (2a-e). Compound (1) reacted with phenyl isothiocyanate to yield the corresponding non-isolable intermediate (3), which gave, upon treatment with dilute hydrochloric acid, thiocarb...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2010-03, Vol.185 (3), p.526-536
Main Authors: Fadda, A. A., Etman, H. A., Sarhan, A. A., El-Hadidy, Sherihan A.
Format: Article
Language:English
Subjects:
1,2,3,4-tetrahydrocarbazole
Aromatic amines
Derivatives
ethyl bromoacetate
phenacyl bromide
phenylisothiocyanate
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Summary:2-Cyano-N-(tetrahydrocarbazole)acetamide (1) was utilized for the synthesis of several new arylazocarbazole derivatives (2a-e). Compound (1) reacted with phenyl isothiocyanate to yield the corresponding non-isolable intermediate (3), which gave, upon treatment with dilute hydrochloric acid, thiocarbamoyl derivative (4). Compound (3) reacted with chloroacetone, chloroacetic acid, chloroacetyl chloride, ethyl bromoacetate, and phenacyl bromide to afford thiazolone derivatives (6), (8), and (10), respectively. Compound (1) was heated in the presence of pyridine and/or hydrazine hydrate and/or isatine to give the corresponding tetrahydrocarbazole derivatives (13), (14), and (18), respectively. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500902839863