Abstract: The introduction of an N,N′-trimethylene bridge in the tetrahydroquinoxaline molecule is complicated by cyclization of γ-bromopropyl derivatives of tetrahydroquinoxaline at the carbon atom of the aromatic ring. The reaction of N-R-tetrahydro-quinoxalines (R = H, COCH3) with 1,3-dibromopropane leads to products of cyclization at the aromatic ring (1,2,3,5,6,8,9,10-octahydropyrazino[1,2,3,4-Z,m,n][1, 10]phenanthroline and N-acetyl-1,2,6,7-tetrahydro-3H,5H-pyrido[1,2,3-d,e]quinoxa-line) and to an N-alkylation product [N-acetyl-N′-(γ-bromopropyl)-1,2,3,4-tetra-hydroquinoxaline]. Benzo[f]-1,5-diazabicyclo[3.2.2]nonene is formed in only trace amounts in the cyclization of N-(γ-bromopropyl)tetrahydroquinoxaline and upon heating in HBr can be isomerized with migration of the trimethylene bridge to the aromatic ring. © 1983 Plenum Publishing Corporation.

Cite: Gall' A.A. , Shishkin G.V.
Diazabicycloalkanes with nitrogen atoms in the nodal positions. 9. Intramolecular cyclization of N-(γ-bromopropyl)-tetrahydroquinoxalines and behavior of benzo[f]-1,5-diazabicyclo[3.2.2]nonene in hydrobromic acid
Chemistry of Heterocyclic Compounds. 1983. V.19. N5. P.549-553. DOI: 10.1007/BF00514468 Scopus РИНЦ OpenAlex

Dates:

Published print:

May 1, 1983

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Scopus:	2-s2.0-34250153876
Elibrary:	30917641
OpenAlex:	W1983769738

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