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Synthesis and chemiluminescent activity of 8,9-dihydrobenzo[g] pyridazino[4,5-b]indole-7,10(11H)-diones

โœ Scribed by Masateru Kurumi; Kenji Sasaki; Hiroko Takata; Taiji Nakayama


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

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โœฆ Synopsis


Abstract

Substituted and unsubstituted naphthylamines were transformed into the corresponding triazole derivatives, which were converted to dimethyl 1__H__โ€benz[g]indoleโ€2,3โ€dicarboxylates by photocyclization. The reaction of the diesters with hydrazine hydrate gave the corresponding 8,9โ€dihydrobenzo[g]โ€pyridazino[4,5โ€b]indoleโ€7,10(11__H__)โ€diones (5). One of compounds 5 was found to have chemiluminescent activity similar to luminol.


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## Abstract The molecular structures of the title compounds 3 and 5 were investigated by NMR and Xโ€ray structural methods. The NMR results suggest two equivalent halves for both molecules. The Xโ€ray study shows an approximate mirror plane for 3 and an approximate twofold axis for a significant port