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Synthesis 2010(7): 1107-1112  
DOI: 10.1055/s-0029-1219235
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Chemical Reactivity of New Azaenamines Incorporated the 4,5,6,7-Tetrahydrobenzo[b]thiophene Moiety: 3+3 Atom Combination

Ismail Abdelshafy Abdelhamid*a,b, Elham Sayed Darwisha, Miead Adel Nasraa, Fathy Mohamed Abdel-Gallila, Daisy Hanna Fleitac
a Chemistry Department, Faculty of Science, Cairo University, Giza, A. R. Egypt
Fax: +20(2)35727556; e-Mail: ismail_shafy@yahoo.com;
b Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany
c Chemistry Department, American University in Cairo, Egypt
Further Information

Publication History

Received 17 November 2009
Publication Date:
20 January 2010 (online)

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Abstract

Novel azaenamines incorporating a tetrahydrothiophene moiety were prepared. Michael addition of an azaenamine with α,β-unsaturated nitriles took place to give [1]benzothieno[3′,2′:5,6]pyrimido[1,2-b]pyridazine (thia-triaza-benzo[a]fluorene) derivatives. The condensation with malononitrile resulted in the formation of a [1]benzothieno[3′,2′:5,6]pyrimido[1,2-b]pyridazine-4-carbonitrile. The azaenamine also reacted with aldehydes and piperidine to give Mannich products.

Key words

azaenamine - tetrahydrobenzo[b]thiophene - Michael addition - condensation - Mannich alkylation

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