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Preparation of 6-, 7-, and 8-substituted derivatives of 2-Oxa-1,3,4,10-tetraazacyclopenta[b]fluoren-9-one

✍ Scribed by Larry D. Bratton; Paul C. Unangst; J. Ronald Rubin; Bharat K. Trivedi

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

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✦ Synopsis

Abstract

The preparation of a variety of derivatives of 2‐oxa‐1,3,4,10‐tetraazacyclopenta[b]fluoren‐9‐one 1 is described. A series of substituted indan‐1‐ones were prepared and oxidized with N‐bromosuccinimide and dimethyl sulfoxide to the corresponding ninhydrin derivatives. Cyclization of the ninhydrins with furazan‐3,4‐diamine yielded the target tetracycles. Appropiate choice of substituents in ninhydrins led to a preference for one regioisomer in the target tetracycles. This permitted the synthesis of a variety of 8‐substituted hetero‐cycles. In those instances where isomer formation was possible, structural assignments were confirmed by X‐ray crystallography.

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