Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones

Géza Timári, G. Hajós, András Messmer

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Alkylation of two differently (linearly and angularly) fused pyridoquinazolones 7 and 10 have been investigated. The linear 7 afforded exclusively N‐alkyl derivatives 4, whereas the angular 10 gave both N‐ and O‐alkyl products 5 and 11, respectively depending on the type of the reagent used. Reaction of the new alkylated salts 4, 5, and 11 with nucleophiles was found strongly dependent on the fusion type of the substrates: the reaction of the linear salt 4 led to opening of the pyrimidine moiety, and the angularly fused salts 5, 11 reacted at the pyridine site to give quinazolyldieneamines 17, 19. Regioselectivities of the observed conversions were interpreted on FMO basis.

Original languageEnglish
Pages (from-to)2005-2009
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume27
Issue number7
DOIs
Publication statusPublished - 1990

Fingerprint

Alkylation
Salts
Fused salts
Regioselectivity
Nucleophiles
Fusion reactions
Derivatives
Substrates
pyridine
pyrimidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones. / Timári, Géza; Hajós, G.; Messmer, András.

In: Journal of Heterocyclic Chemistry, Vol. 27, No. 7, 1990, p. 2005-2009.

Research output: Contribution to journalArticle

@article{58b17c4fe3514095bf0bce64206f857c,
title = "Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones",
abstract = "Alkylation of two differently (linearly and angularly) fused pyridoquinazolones 7 and 10 have been investigated. The linear 7 afforded exclusively N‐alkyl derivatives 4, whereas the angular 10 gave both N‐ and O‐alkyl products 5 and 11, respectively depending on the type of the reagent used. Reaction of the new alkylated salts 4, 5, and 11 with nucleophiles was found strongly dependent on the fusion type of the substrates: the reaction of the linear salt 4 led to opening of the pyrimidine moiety, and the angularly fused salts 5, 11 reacted at the pyridine site to give quinazolyldieneamines 17, 19. Regioselectivities of the observed conversions were interpreted on FMO basis.",
author = "G{\'e}za Tim{\'a}ri and G. Haj{\'o}s and Andr{\'a}s Messmer",
year = "1990",
doi = "10.1002/jhet.5570270730",
language = "English",
volume = "27",
pages = "2005--2009",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "7",

}

TY - JOUR

T1 - Synthesis, alkylation and ring opening of two differently fused pyridoquinazolones

AU - Timári, Géza

AU - Hajós, G.

AU - Messmer, András

PY - 1990

Y1 - 1990

N2 - Alkylation of two differently (linearly and angularly) fused pyridoquinazolones 7 and 10 have been investigated. The linear 7 afforded exclusively N‐alkyl derivatives 4, whereas the angular 10 gave both N‐ and O‐alkyl products 5 and 11, respectively depending on the type of the reagent used. Reaction of the new alkylated salts 4, 5, and 11 with nucleophiles was found strongly dependent on the fusion type of the substrates: the reaction of the linear salt 4 led to opening of the pyrimidine moiety, and the angularly fused salts 5, 11 reacted at the pyridine site to give quinazolyldieneamines 17, 19. Regioselectivities of the observed conversions were interpreted on FMO basis.

AB - Alkylation of two differently (linearly and angularly) fused pyridoquinazolones 7 and 10 have been investigated. The linear 7 afforded exclusively N‐alkyl derivatives 4, whereas the angular 10 gave both N‐ and O‐alkyl products 5 and 11, respectively depending on the type of the reagent used. Reaction of the new alkylated salts 4, 5, and 11 with nucleophiles was found strongly dependent on the fusion type of the substrates: the reaction of the linear salt 4 led to opening of the pyrimidine moiety, and the angularly fused salts 5, 11 reacted at the pyridine site to give quinazolyldieneamines 17, 19. Regioselectivities of the observed conversions were interpreted on FMO basis.

UR - http://www.scopus.com/inward/record.url?scp=3643143149&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=3643143149&partnerID=8YFLogxK

U2 - 10.1002/jhet.5570270730

DO - 10.1002/jhet.5570270730

M3 - Article

VL - 27

SP - 2005

EP - 2009

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 7

ER -