Diazabicycloalkanes with nitrogen atoms in the nodal positions. 10. Intramolecular cyclization of β-bromoethyl-and γ-bromopropyl-N,N′-alkylene-o-phenylenediamines

Diazabicycloalkanes with nitrogen atoms in the nodal positions. 10. Intramolecular cyclization of β-bromoethyl-and γ-bromopropyl-N,N′-alkylene-o-phenylenediamines Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 1983, Volume: 19, Number: 5, Pages: 553-558 Pages count : DOI: 10.1007/BF00514469

Authors

Gall' A. A. , Shishkin G. V.

Affiliations

1	(Scopus) Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk, 630090, Russian Federation

The overall scheme of the intramolecular cyclization of bromoalkyl derivatives of N,N′-alkylene-o-phenylenediamines in HBr was established, and the rates of the individual steps of this complex process were estimated. It is shown that N-(β-bromoethyl)-N,N′-trimethylene-o-phenylenediamine undergoes virtually irreversible cyclization at a high rate to give benzo[f]-1,5-diazabicyclo[3.2.2]-nonene in significant yield, while the cyclization of N-(γ-bromopropyl)-1,2,3, 4-tetrahydroquinoxaline proceeds at commensurable rates via two pathways, viz., C- and N-alkylation. This makes it impossible to use the latter reaction to obtain benzo[f]-1,5-diazabicyclo[3.2.2]nonene in high yield. © 1983 Plenum Publishing Corporation.

Gall' A.A. , Shishkin G.V.
Diazabicycloalkanes with nitrogen atoms in the nodal positions. 10. Intramolecular cyclization of β-bromoethyl-and γ-bromopropyl-N,N′-alkylene-o-phenylenediamines
Chemistry of Heterocyclic Compounds. 1983. V.19. N5. P.553-558. DOI: 10.1007/BF00514469 Scopus РИНЦ OpenAlex

Published print:

May 1, 1983

Scopus:	2-s2.0-34250143124
Elibrary:	30988865
OpenAlex:	W1989828719

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