Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines

László Pongó, B. Ágai, F. Faigl, József Reiter, Gyula Simig

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

o-Aroylarylacetone type 1,5-diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3-dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9-Dialkoxy-2,3- benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8-dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N-amino-7,8-dialkoxyisoquinolinium chlorides (10) and 7,8-dialkoxyisoquinolinium oxides (12), respectively.

Original languageEnglish
Pages (from-to)1539-1548
Number of pages10
JournalJournal of Heterocyclic Chemistry
Volume43
Issue number6
DOIs
Publication statusPublished - Nov 2006

Fingerprint

hydrazine
Chlorides
Acylation
Hydroxylamine
Cyclization
Benzodiazepines
Ammonia
Oxides
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines. / Pongó, László; Ágai, B.; Faigl, F.; Reiter, József; Simig, Gyula.

In: Journal of Heterocyclic Chemistry, Vol. 43, No. 6, 11.2006, p. 1539-1548.

Research output: Contribution to journalArticle

Pongó, László ; Ágai, B. ; Faigl, F. ; Reiter, József ; Simig, Gyula. / Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines. In: Journal of Heterocyclic Chemistry. 2006 ; Vol. 43, No. 6. pp. 1539-1548.
@article{b471bb73b8d64ec690726ce896476a1e,
title = "Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines",
abstract = "o-Aroylarylacetone type 1,5-diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3-dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9-Dialkoxy-2,3- benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8-dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N-amino-7,8-dialkoxyisoquinolinium chlorides (10) and 7,8-dialkoxyisoquinolinium oxides (12), respectively.",
author = "L{\'a}szl{\'o} Pong{\'o} and B. {\'A}gai and F. Faigl and J{\'o}zsef Reiter and Gyula Simig",
year = "2006",
month = "11",
doi = "10.1002/jhet.5570430617",
language = "English",
volume = "43",
pages = "1539--1548",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "6",

}

TY - JOUR

T1 - Synthesis of 8,9-dialkoxybenzodiazepines and 7,8-dialkoxyisoquinolines

AU - Pongó, László

AU - Ágai, B.

AU - Faigl, F.

AU - Reiter, József

AU - Simig, Gyula

PY - 2006/11

Y1 - 2006/11

N2 - o-Aroylarylacetone type 1,5-diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3-dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9-Dialkoxy-2,3- benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8-dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N-amino-7,8-dialkoxyisoquinolinium chlorides (10) and 7,8-dialkoxyisoquinolinium oxides (12), respectively.

AB - o-Aroylarylacetone type 1,5-diketone derivatives (5, 6) were synthesised from arylacetones (1) protected as 1,3-dioxolanes (4) through directed ortho lithiation followed by acylation with aroyl chlorides. 8,9-Dialkoxy-2,3- benzodiazepines 9 were obtained by cyclisation of diketones 6 with hydrazine. The reaction of diketones 6 with ammonia gave 7,8-dialkoxyisoquinolines 11. Reaction of ketals 5 with hydrazine hydrochloride and hydroxylamine hydrochloride afforded N-amino-7,8-dialkoxyisoquinolinium chlorides (10) and 7,8-dialkoxyisoquinolinium oxides (12), respectively.

UR - http://www.scopus.com/inward/record.url?scp=33845447619&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845447619&partnerID=8YFLogxK

U2 - 10.1002/jhet.5570430617

DO - 10.1002/jhet.5570430617

M3 - Article

AN - SCOPUS:33845447619

VL - 43

SP - 1539

EP - 1548

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 6

ER -