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Synthesis 2011(18): 3006-3014  
DOI: 10.1055/s-0030-1261033
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Effective Suzuki-Miyaura Arylation and Sonogashira Aryl Alkynylation on N-Heteroaromatic Cations: Synthesis of Substituted Pyridine-Fused Cationic Heterocycles

Rupankar Paira, Krishnendu B. Sahu, Shyamal Mondal, Arindam Maity, Abhijit Hazra, Subhendu Naskar, Pritam Saha, E. Padmanaban, Sukdeb Banerjee, Nirup B. Mondal*
Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata-700032, India
Fax: +91(33)24735197; e-Mail: nirup@iicb.res.in;
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Publication History

Received 15 June 2011
Publication Date:
05 August 2011 (online)

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Abstract

Suzuki-Miyaura and Sonogashira cross-coupling reactions were efficiently employed for the syntheses of aryl, biaryl, and aryl alkynyl substituted polycyclic tetrahydropyrimidinium, di­azepanium, and diazocanium derivatives with moderate-to-high yields. Appropriately functionalized pyridinium templates for these syntheses were obtained under microwave irradiation, using basic alumina as the solid support.

Key words

Suzuki-Miyaura - Sonogashira - cross-coupling - fused rings - diazepanium - diazocanium

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