Synthesis of some thiophene-fused azepino[5,4,3 -cd]indoles

Basem A. Moosa; Kayed A. Abu Safieh; Mustafa M. El-Abadelah

doi:10.3987/com-02-9551

Synthesis of some thiophene-fused azepino[5,4,3 -cd]indoles

Basem A. Moosa^*, Kayed A. Abu Safieh, Mustafa M. El-Abadelah

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxychloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2′,3′: 6,7]azepino[5,4,3-cd]indoles (3a-c).

Original language	English (US)
Pages (from-to)	1831-1840
Number of pages	10
Journal	Heterocycles
Volume	57
Issue number	10
DOIs	https://doi.org/10.3987/com-02-9551
State	Published - Oct 1 2002
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxychloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2′,3′: 6,7]azepino[5,4,3-cd]indoles (3a-c).",

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T1 - Synthesis of some thiophene-fused azepino[5,4,3 -cd]indoles

AU - Moosa, Basem A.

AU - Abu Safieh, Kayed A.

AU - El-Abadelah, Mustafa M.

PY - 2002/10/1

Y1 - 2002/10/1

N2 - Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxychloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2′,3′: 6,7]azepino[5,4,3-cd]indoles (3a-c).

AB - Interaction of indolylzinc chloride with 2-chloro-3-nitrothiophene gave 3-(3-nitrothien-2-yl)indole (7) which was converted, via reduction followed by acylation, into 3-(3-acylaminothien-2-yl)indoles (9a-c). Cyclization of 9a-c induced by phosphorus oxychloride under Bischler-Napieralski reaction conditions, took place regioselectively at the indolic C-4 locus to furnish the respective thieno[2′,3′: 6,7]azepino[5,4,3-cd]indoles (3a-c).

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DO - 10.3987/com-02-9551

M3 - Article

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JO - Heterocycles

JF - Heterocycles

IS - 10

ER -

Synthesis of some thiophene-fused azepino[5,4,3 -cd]indoles

Abstract

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