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

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 185; no. 3; pp. 526 - 536
• Main Authors: Fadda, A. A., Etman, H. A., Sarhan, A. A., El-Hadidy, Sherihan A.
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis Group 01.03.2010; Taylor & Francis; Taylor & Francis Ltd
• Subjects: 1,2,3,4-tetrahydrocarbazole; Aromatic amines; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Derivatives; ethyl bromoacetate; phenacyl bromide; phenylisothiocyanate; Physical Sciences; Science & Technology; 1; phenylisothiocyanate; 2; Aromatic amines; 3; 4-tetrahydrocarbazole; phenacyl bromide; ethyl bromoacetate
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500902839863

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.