Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 27, No. 7, 1988, pp.1607-1614
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4587
Synthesis of 7,12-Dihydropyridopyrroloindoles (Azapyridodiindoles) via the Fischer Indole Cyclization. A Search for Water Soluble Benzodiazepine Receptor Ligands.

Yun-chou Tan, Mark L. Trudell, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


The thermally-induced Fischer indole cyclization of the 3-acylindole 7 with various substituted hydrazinopyridines provides a simple route to the 7,12-dihydropyridopyrroloindoles 2, 4 and 5, respectively. In contrast, the corresponding acid-catalyzed process yielded only 4-amino-β-carboline 15. Moreover, attempts to prepare the 3-aza-analog 3, from reaction of 7 and 4-hydrazinopyridine 12 under thermal or acidic conditions, provided only 15. The difference between the reactivity of the 4-substituted pyridine 12, in comparison to 11 or 13, is discussed in terms of pKa values and intermediates in the Fischer indole cyclization.