Reaction of 1,2‐Dialkyldiaziridines and 1,2,3‐Trialkyldiaziridines with Methyl Propiolate in Ionic Liquids and in Organic Solvents

Reaction of 1,2‐Dialkyldiaziridines and 1,2,3‐Trialkyldiaziridines with Methyl Propiolate in Ionic Liquids and in Organic Solvents Full article

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Output data

Year: 2013, Volume: 50, Number: 2, Pages: 326-336 Pages count : 11 DOI: 10.1002/jhet.1079

Authors

Petukhova Vera Yu. ¹ , Fershtat Leonid L. ¹ , Kachala Vadim V. ¹ , Kuznetsov Vladimir V. ¹ , Khakimov Dmitriy V. ¹ , Pivina Tatyana S. ¹ , Makhova Nina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation

An interaction of 1,2-dialkyldiaziridine and 1,2,3-trialkyldiaziridine with methyl propiolate was studied both in organic solvent (MeCN, CH2Cl2, C6H6) 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.

Petukhova V.Y. , Fershtat L.L. , Kachala V.V. , Kuznetsov V.V. , Khakimov D.V. , Pivina T.S. , Makhova N.N.
Reaction of 1,2‐Dialkyldiaziridines and 1,2,3‐Trialkyldiaziridines with Methyl Propiolate in Ionic Liquids and in Organic Solvents
Journal of Heterocyclic Chemistry. 2013. V.50. N2. P.326-336. DOI: 10.1002/jhet.1079 WOS Scopus OpenAlex

Web of science:	WOS:000318293000024
Scopus:	2-s2.0-84876892435
OpenAlex:	W2950521791

DB	Citing
OpenAlex	11
Scopus	10
Web of science	9