Reaction of Nitrilimines with 2-Substituted Aza-heterocycles. Synthesis of Pyrrolo[1,2-a]pyridine and Pyrimido[2,1-d]1,2,3,5- tetrazine 英文参考文献.docVIP

Molecules 2008, 13, 170-176 molecules ISSN 1420-3049 ? 2008 by MDPI /molecules Full Paper Reaction of Nitrilimines with 2-Substituted Aza-heterocycles. Synthesis of Pyrrolo[1,2-a]pyridine and Pyrimido[2,1-d]1,2,3,5- tetrazine Adel M. Awadallah 1,* and Jalal A. Zahra 2 1 Chemistry Department, Faculty of Science, Islamic University of Gaza, P. O. Box 108, Gaza, Palestine 2 Chemistry Department, Faculty of Science, University of Jordan, Amman, Jordan; E-mail: zahra@.jo; Fax: +962-6 5348932; Tel.: +962-6 5355000 (ext. 22163) * Author to whom correspondence should be addressed; E-mail: awada@.ps; Tel. +970-8-2823311, Fax: +970-8-2823310 Received: 9 January 2008; in revised form: 22 January 2008 / Accepted: 22 January 2008 / Published: 28 January 2008 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. Keywords: Nitrilimines, ethyl pyridine-2-acetate, pyrrolo[1,2-a]pyridine, 2-amino- pyrimidine, pyrimido[2,1-d]1,2,3,5-tetrazine, 2-cyanomethylbenzimidazole, 2-amino- benzimidazole Introduction 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. They are used as 5- lipoxygenase pathway inhibitors [1]. Their uses for different purposes, including their interesting  Molecules 2008, 13 171 biological activities, were summarized by Wang et al. [2]. Recently, Gundersen et al. reported the synthesis of indolizine derivatives with selective antibacte