Acid-Catalyzed Reactions of 3-Substituted-4,6-dimethoxyindoles with Ketones-Reference-Cited by-同舟云学术

Acid-Catalyzed Reactions of 3-Substituted-4,6-dimethoxyindoles with Ketones

Published:2010 Issue:5 Volume:63 Page:761
ISSN:0004-9425
Container-title:Australian Journal of Chemistry
language:en
Short-container-title:Aust. J. Chem.

Author:

Wood Kasey,Black David StC.,Kumar Naresh

Abstract

Activated 3-substituted-4,6-dimethoxyindoles undergo acid catalyzed condensation with acetone and acetophenones in the presence of hydrochloric acid to give pyrrolo[a]indoles. Mixed pyrrolo[a]indoles can similarly be formed using a 1:1 mixture of two indoles. The reaction was found to be sensitive to acidity, with a 3:2 spiro condensation product being preferentially formed in the presence of p-toluenesulfonic acid.

Publisher

CSIRO Publishing

Subject

General Chemistry

Link

https://www.publish.csiro.au/CH/pdf/CH10137

Reference28 articles.

1. Spermacoceine, a bis-indole alkaloid from Borreria verticillata

2. Yuehchukene: a novel indole alkaloid with anti-implantation activity

3. Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives

4. Structure-function relationship of Yuehchukene II. The effect of C-6 indole rotation on anti-implantation activity

5. Antifertility agents: synthesis of yuehchukene analogues: 6β-(indol-3-yl)-9,12-dimethyl-6,7,10,11-tetrahydro-7,11-methano-5H-[b]indole and 6β-(indol-3-yl)-9,12-dimethyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-oct[b]indole

Cited by 6 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Organocatalytic Michael Addition of Indoles to α-Substituted Enals by Using a Diazepane Carboxylate Catalyst;European Journal of Organic Chemistry;2017-05-10

2. Reactions of Aldehydes and Ketones and their Derivatives;Organic Reaction Mechanisms Series;2012-12-04

3. One-Pot Synthesis of Asymmetric Annulated Bis(pyrrole)s;Organic Letters;2011-10-12

4. Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1H-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1H-Pyrrolo[1,2-a]indoles;Organic Letters;2011-10-11

5. ChemInform Abstract: Acid-Catalyzed Reactions of 3-Substituted-4,6-dimethoxyindoles with Ketones.;ChemInform;2010-10-25