Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/111735
Title: New Transformations of N-hetarylcyclopentano[d][1,2,3]triazoline Ring into 5-alkoxyvaleramidines
Authors: Belyaev, N. A.
Beryozkina, T. V.
Lubec, G.
Dehaen, W.
Bakulev, V. A.
Issue Date: 2018
Publisher: Springer New York LLC
Springer Science and Business Media LLC
Citation: New Transformations of N-hetarylcyclopentano[d][1,2,3]triazoline Ring into 5-alkoxyvaleramidines / N. A. Belyaev, T. V. Beryozkina, G. Lubec et al. // Chemistry of Heterocyclic Compounds. — 2018. — Vol. 54. — Iss. 11. — P. 1050-1055.
Abstract: [Figure not available: see fulltext.] 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. © 2018, Springer Science+Business Media, LLC, part of Springer Nature.
Keywords: AMIDINES
IMIDAZOLES
PYRIMIDINEDIONES
RING TRANSFORMATIONS
TRANSLATED FROM KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2018, 54(11), 1050–1055
TRIAZINES
TRIAZOLINES
URI: http://hdl.handle.net/10995/111735
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85058692331
PURE ID: 8873324
ISSN: 0009-3122
metadata.dc.description.sponsorship: This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 18-03-00715).
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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