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Synthesis 2017; 49(16): 3720-3725
DOI: 10.1055/s-0036-1588179
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© Georg Thieme Verlag Stuttgart · New York

Eschenmoser Coupling Reaction and Reactivity of Hydrazinecarbo­thioamides in the Synthesis of Benzindazole and Naphthothiazole Derivatives

Alaa A. Hassan*
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt
,
Nasr K. Mohamed
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt
,
Kamal M. A. El-Shaieb
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt
,
Hendawy N. Tawfeek
a   Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, A. R. Egypt
,
Stefan Bräse
b   Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
,
Martin Nieger
c   Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasenaukio I), 00014 University of Helsinki, Finland   Email: alaahassan2001@mu.edu.eg
› Author Affiliations
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Publication History

Received: 07 March 2017

Accepted after revision: 25 April 2017

Publication Date:
24 May 2017 (online)

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Abstract

N-Unsubstituted and N-substituted 2-phenylhydrazinecarbothioamides react with 2,3-dichloro-1,4-naphthoquinone to give a series of unprecedented 3-amino- and 3-(alkylamino)-1-phenyl-1H-benzo[f]indazole-4,9-diones in good yields. On the other hand, the reaction of N-substituted 2-tosylhydrazinecarbothioamides with 2,3-dichloro-1,4-naphthoquinone afforded (Z)-N-[3-(tosylamino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-2(3H)-ylidene]-substituted aminium chlorides and (Z)-N-[(2-substituted imino)-4,9-dioxo-4,9-dihydronaphtho[2,3-d]thiazol-3(2H)-yl]-4-toluenesulfonamide hydrates.

Key words

hydrazinecarbothioamides - 2,3-dichloro-1,4-naphtho­quinone - benzo[f]indazole-4,9-diones - naphtho[2,3-d]thiazoles - Eschenmoser­ reaction

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