Nitrogen bridgehead compounds. Part 88. Synthesis of 3H,7H-[1,4]diazepino[3,4-b]quinazoline-3,7-diones

M. Szabo, J. Kökösi, L. Őrfi, A. Kovacs, I. Hermecz

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Abstract

3H,7H-[1,4]Diazepino[3,4-b]quinazolone-3,7-diones 9, 11 were synthesized starting from 2-(1-bromoethyl)quinazolin-4(3H)-ones 3 and 17 via 2-[1-(4-methoxyphenylamino)ethyl]quinazolin-4(3H)-ones 4 and 18. Cyclization of 3-[2-(1-bromoethyl)-4-oxo-3,4-dihydroquinazolin-3-yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7H-[1,4]oxazepino[3,4-b]quinazoline-3,7-dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1H nmr spectroscopy.

Original languageEnglish
Pages (from-to)21-25
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume34
Issue number1
Publication statusPublished - 1997

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Quinazolines
Nitrogen Compounds
Cyclization
Spectroscopy
Derivatives
propionic acid
triethylamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Nitrogen bridgehead compounds. Part 88. Synthesis of 3H,7H-[1,4]diazepino[3,4-b]quinazoline-3,7-diones",
abstract = "3H,7H-[1,4]Diazepino[3,4-b]quinazolone-3,7-diones 9, 11 were synthesized starting from 2-(1-bromoethyl)quinazolin-4(3H)-ones 3 and 17 via 2-[1-(4-methoxyphenylamino)ethyl]quinazolin-4(3H)-ones 4 and 18. Cyclization of 3-[2-(1-bromoethyl)-4-oxo-3,4-dihydroquinazolin-3-yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7H-[1,4]oxazepino[3,4-b]quinazoline-3,7-dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1H nmr spectroscopy.",
author = "M. Szabo and J. K{\"o}k{\"o}si and L. Őrfi and A. Kovacs and I. Hermecz",
year = "1997",
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journal = "Journal of Heterocyclic Chemistry",
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T1 - Nitrogen bridgehead compounds. Part 88. Synthesis of 3H,7H-[1,4]diazepino[3,4-b]quinazoline-3,7-diones

AU - Szabo, M.

AU - Kökösi, J.

AU - Őrfi, L.

AU - Kovacs, A.

AU - Hermecz, I.

PY - 1997

Y1 - 1997

N2 - 3H,7H-[1,4]Diazepino[3,4-b]quinazolone-3,7-diones 9, 11 were synthesized starting from 2-(1-bromoethyl)quinazolin-4(3H)-ones 3 and 17 via 2-[1-(4-methoxyphenylamino)ethyl]quinazolin-4(3H)-ones 4 and 18. Cyclization of 3-[2-(1-bromoethyl)-4-oxo-3,4-dihydroquinazolin-3-yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7H-[1,4]oxazepino[3,4-b]quinazoline-3,7-dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1H nmr spectroscopy.

AB - 3H,7H-[1,4]Diazepino[3,4-b]quinazolone-3,7-diones 9, 11 were synthesized starting from 2-(1-bromoethyl)quinazolin-4(3H)-ones 3 and 17 via 2-[1-(4-methoxyphenylamino)ethyl]quinazolin-4(3H)-ones 4 and 18. Cyclization of 3-[2-(1-bromoethyl)-4-oxo-3,4-dihydroquinazolin-3-yl)propionic acid 14 by the action of triethylamine provided the first representative of the tricyclic 7H-[1,4]oxazepino[3,4-b]quinazoline-3,7-dione system, compound 15. The new tricyclic derivatives 9, 11 and 15 are characterized by uv, ir and 1H nmr spectroscopy.

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