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NEW TRANSFORMATIONS OF N-HETARYLCYCLOPENTANO[d][1,2,3]TRIAZOLINE RING INTO 5-ALKOXYVALERAMIDINES

Николай А. Беляев, Татьяна В. Березкина, Герт Любек, Вим Дэхан, Василий А. Бакулев
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Abstract


It was found that brief refluxing of N-hetarylcyclopentano[d][1,2,3]triazolines in methanol resulted in the elimination of nitrogen, accompanied by cyclopentane ring opening with the formation of N-hetarylvaleramidines. Amidines containing pyrimidine-2,4-dione ring were synthesized by a one-step procedure – the reaction of 5-azidopyrimidine-2,4-diones with endocyclic enamines containing a cyclopentene ring proceeded through an N-pyrimidyl-1,2,3-triazoline intermediate. Triazolines containing a 1,3,5-triazine ring at  position 1 did not form valeramidines upon refluxing in methanol. N-(1,3,5-triazin-2-yl)cyclopenta[d][1,2,3]triazoline containing a morpholine ring at position 6a underwent a different type of transformation upon dissolving in acetic acid, resulting in the formation of N-(1,3,5-triazin-2-yl)diaminoalkene. Mechanisms for these transformations are proposed.

Authors: Nikolay A. Belyaev, Tetyana V. Beryozkina, Gert Lubec,
Wim Dehaen, Vasiliy A. Bakulev

 


Keywords


amidines; imidazoles; pyrimidinediones; triazines; triazolines; ring transformations

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