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Reaction of 1,2‐Dialkyldiaziridines and 1,2,3‐Trialkyldiaziridines with Methyl Propiolate in Ionic Liquids and in Organic Solvents
Author(s) -
Petukhova Vera Yu.,
Fershtat Leonid L.,
Kachala Vadim V.,
Kuznetsov Vladimir V.,
Khakimov Dmitriy V.,
Pivina Tatyana S.,
Makhova Ni.
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1079
Subject(s) - chemistry , ionic liquid , regioselectivity , adduct , molecule , ionic bonding , ring (chemistry) , computational chemistry , solvent , quantum chemical , organic chemistry , medicinal chemistry , ion , catalysis
An interaction of 1,2‐dialkyldiaziridine and 1,2,3‐trialkyldiaziridine with methyl propiolate was studied both in organic solvent (MeCN, CH 2 Cl 2 , C 6 H 6 ) and in ionic liquids . Earlier unknown linear structures, in which three molecules of methyl propiolate were suited to one diaziridine molecule (adducts 1 : 3), were obtained in MeCN. The diaziridine ring expansion products 1,2,3,4‐tetrahydropyrimidine derivatives (adducts 1 : 2) and, along with them in some cases, the same linear structures were obtained in ionic liquids . A mechanism of reactions found was offered. The regioselectivity of reactions was supposed to determine by the structure of substituents in initial diaziridines. This conclusion was supported by quantum chemical calculations.