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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.

Abstract

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.