Abstract
The reaction of nitrilimine 6a with ethyl pyridine-2-acetate (7) gave the corresponding pyrrolo[1,2-a]pyridine 8, while the reaction of 6b containing an ester moiety afforded the acyclic adduct 9. The reaction of 6a with 2-aminopyrimidine (10) gave the novel unexpected pyrimido[2,1-d]1,2,3,5-tetrazine 11. Acyclic adducts 16 and 17 were obtained from the reaction of 6b with 2-cyanomethylbenzimidazole (14) and 2-aminobenzimidazole (15), respectively.
Highlights
Pyrrolo[1,2-a]pyridine derivatives possess a wide range of physiological activity, which depend on the nature of the substituents and their position on the molecule
Gundersen et al reported the synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis [3]
Indolizine derivatives can be prepared by different routes, including the 1,3-dipolar cycloaddition reaction of pyridylnitrilimines with dimethyl acetylenedicarboxylate [4]. 1,3-Dipolar cycloadditions of pyridinium N-ylides to alkenes were used for their preparation [2]
Summary
Pyrrolo[1,2-a]pyridine (inolizine) derivatives possess a wide range of physiological activity, which depend on the nature of the substituents and their position on the molecule. Indolizine derivatives can be prepared by different routes, including the 1,3-dipolar cycloaddition reaction of pyridylnitrilimines with dimethyl acetylenedicarboxylate [4]. The synthesis of different fused heterocyclic systems was recently reported using nitrilimines and 2-substituted aza-heterocycles.
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