A Facile Construction of the Benz[c,d]indole Framework
Year: 2006
Type: article
Abstract: The Bradsher cycloaddition of isoquinolinium salts has been applied to 5-acetaminoisoquinoline.In 3 simple steps: (i) quaternization of isoquinoline N (ii) cycloaddition with electron-rich dienophile (iii) dehydration, the benz[c,d]indole framework is formed.The indole ring system has been at the top of the list of privileged substructures in medicinal chemistry. 1e same can be said for the benz [c,d]indole framework 1 exemplified by lysergic acid diethylamide (2). 2In the new era of synthesis where a premium is placed on diversity-oriented programs (as compared to target-oriented approaches), indoles are no exception. 3,4In this report, we describe the first steps in the development of a benz [c,d]indole synthesis via Bradsher cycloaddition chemistry that has the potential for diversity.
Source: Heterocycles
DOI: 10.3987/com-06-s(w)1
Authors: Richard W. Franck, Clifford E. Soll
Institution: Hunter College
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2951600906