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.
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.
Branowska
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Institute of Chemistry, University of Podlasie, PL-08-110 Siedlce, Poland. dankab@ap.siedlce.pl
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008954:Models, Biological; D008956:Models, Chemical; D010880:Piperidines / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
D003516:Cycloparaffins; D006571:Heterocyclic Compounds; D010880:Piperidines; D014227:Triazines; D015082:2,2'-Dipyridyl