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Molecules 2005, 10(1), 265-273; doi:10.3390/10010265
Article

Synthesis of Unsymmetrical Annulated 2,2’-Bipyridine Analogues with Attached Cycloalkene and Piperidine Rings via Sequential Diels-Alder Reaction of 5,5’-bi-1,2,4-triazines†

Institute of Chemistry, University of Podlasie, Poland
Received: 5 September 2004 / Accepted: 22 September 2004 / Published: 31 December 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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Abstract

Synthesis of bisfunctionalized unsymmetrical 2,2’-bipyridines 8 or their sulfonyl derivatives 12a,b are described. They were prepared via the Diels-Alder reaction of 1-methyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (6) with 3,3’-bis(methyl- sulfanyl)-5,5’-bi-1,2,4-triazine (1). The reaction leads to the single cycloaddition product 7 which undergoes Diels-Alder reaction with cyclic enamines 2a,b to give unsymmetrical 2,2’-bipyridine derivatives 8, consisting of the two different heterocyclic units: cycloalkeno[c]pyridine and 2,6-naphthyridine.
Keywords: bi-1; 2; 4-Triazines; Diels-Alder reaction; isocyclic and heterocyclic enamines bi-1; 2; 4-Triazines; Diels-Alder reaction; isocyclic and heterocyclic enamines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Branowska, D. Synthesis of Unsymmetrical Annulated 2,2’-Bipyridine Analogues with Attached Cycloalkene and Piperidine Rings via Sequential Diels-Alder Reaction of 5,5’-bi-1,2,4-triazines†. Molecules 2005, 10, 265-273.

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