Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4- c]quinazoline derivatives

Renáta Csütörtöki, I. Szatmári, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, F. Fülöp

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A new highly functionalized aminonaphthol derivative, 1-(amino(2- aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde, benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.

Original languageEnglish
Pages (from-to)8564-8571
Number of pages8
JournalTetrahedron
Volume67
Issue number44
DOIs
Publication statusPublished - Nov 4 2011

Fingerprint

Quinazolines
2-nitrobenzaldehyde
Carbamates
Phosgene
Derivatives
Formaldehyde
Magnetic Resonance Spectroscopy
Molecular modeling
Nuclear magnetic resonance spectroscopy
2-naphthol
benzaldehyde

Keywords

  • Conformational analysis
  • DFT calculations
  • Hammett-Brown plots
  • Naphthoxazinoquinazolines
  • NMR

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4- c]quinazoline derivatives. / Csütörtöki, Renáta; Szatmári, I.; Koch, Andreas; Heydenreich, Matthias; Kleinpeter, Erich; Fülöp, F.

In: Tetrahedron, Vol. 67, No. 44, 04.11.2011, p. 8564-8571.

Research output: Contribution to journalArticle

Csütörtöki, Renáta ; Szatmári, I. ; Koch, Andreas ; Heydenreich, Matthias ; Kleinpeter, Erich ; Fülöp, F. / Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4- c]quinazoline derivatives. In: Tetrahedron. 2011 ; Vol. 67, No. 44. pp. 8564-8571.
@article{4d37f5cf6c22418dbbe8f7f9fc457d62,
title = "Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4- c]quinazoline derivatives",
abstract = "A new highly functionalized aminonaphthol derivative, 1-(amino(2- aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde, benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.",
keywords = "Conformational analysis, DFT calculations, Hammett-Brown plots, Naphthoxazinoquinazolines, NMR",
author = "Ren{\'a}ta Cs{\"u}t{\"o}rt{\"o}ki and I. Szatm{\'a}ri and Andreas Koch and Matthias Heydenreich and Erich Kleinpeter and F. F{\"u}l{\"o}p",
year = "2011",
month = "11",
day = "4",
doi = "10.1016/j.tet.2011.08.074",
language = "English",
volume = "67",
pages = "8564--8571",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "44",

}

TY - JOUR

T1 - Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4- c]quinazoline derivatives

AU - Csütörtöki, Renáta

AU - Szatmári, I.

AU - Koch, Andreas

AU - Heydenreich, Matthias

AU - Kleinpeter, Erich

AU - Fülöp, F.

PY - 2011/11/4

Y1 - 2011/11/4

N2 - A new highly functionalized aminonaphthol derivative, 1-(amino(2- aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde, benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.

AB - A new highly functionalized aminonaphthol derivative, 1-(amino(2- aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde, benzaldehyde and/or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.

KW - Conformational analysis

KW - DFT calculations

KW - Hammett-Brown plots

KW - Naphthoxazinoquinazolines

KW - NMR

UR - http://www.scopus.com/inward/record.url?scp=80053261616&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80053261616&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2011.08.074

DO - 10.1016/j.tet.2011.08.074

M3 - Article

VL - 67

SP - 8564

EP - 8571

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 44

ER -