𝔖 Bobbio Scriptorium
✦   LIBER   ✦

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

✍ Scribed by Kayed A. Abu Safieh; Mustafa M. El-Abadelah; Musa H. Abu Zarga; Salim S. Sabri; Wolfgang Voelter; Cäcilia M. MÖssmer

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
76 KB
Volume
38
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis of some new pyrazolo[3′,4′:6,7]azepino[5,4,3‐cd] indoles (10a‐c) was achieved via regios‐elective cyclization of the respective 3‐(4‐acylaminopyrazol‐5‐yl)indoles (9a‐c) under Bischler‐Napieralski reaction conditions. The latter compounds were obtained by acylation of the corresponding 3‐(4‐aminopyra‐zol‐5‐yl)indoles (8a,b) which, in turn, were prepared by reduction of the 3‐(4‐nitropyrazol‐5‐yl)indoles precursors (7a,b). The latter synthons were accessible from the reaction of indolylzinc chlorides (5a,b) with 5‐chloro‐1,3‐dimethyl‐4‐nitropyrazole. Ms and nmr spectral data of 10a‐c are in agreement with the assigned azepino‐indole structure as determined for 10a by X‐ray crystal measurements which demonstrate that the azepine ring is almost completely planar with the indole and pyrazole rings.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of Pyrazo
ChemInform Abstract: Synthesis of Pyrazole-Fused Azepino[5,4,3-cd]indoles.
✍ Kayed A. Abu Safieh; Mustafa M. El-Abadelah; Salim S. Sabri; Musa H. Abu Zarga; 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Synthesis of pyrrolo[3′,4′:2,3]azepino[4
Synthesis of pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones
✍ Siavosh Mahboobi; Stella Eluwa; Markus Koller; Alfred Popp; Dieter Schollmeyer 📂 Article 📅 2000 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 679 KB

## Abstract 3‐Amino‐4‐(3‐indolyl)pyrrolin‐2,5‐diones are condensed with various aldehydes and ketones to the cor responding imines. Under Pictet‐Spengler conditions, the latter do not cyclize to pyrrolo‐β‐carbolines, but readily yield pyrrolo[3′,4′:2,3]azepino[4,5,6‐__cd__]indole‐8,10‐diones.