Remarkable regioselectivities in the course of the synthesis of two new Luotonin A derivatives

Mohamed Atia, Dóra Bogdán, Maryam Brügger, Norbert Haider, P. Mátyus

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate reacts selectively with trimethylaluminium-activated 2-amino- or 4-aminobenzoic acid ethyl esters to give the corresponding anilides without self-condensation of the aminobenzoate building blocks. After propargylation, the quinazolinones were treated with Hendrickson's reagent, but only the para-substituted ester was found to undergo the expected [4 + 2] cycloaddition reaction, affording a new Luotonin A derivative. A different regioselectivity was observed with the ortho-substituted ester which affords a benzoxazinone under identical conditions. When the ester group in the ortho-substituted intermediate is replaced with a nitrile function, the outcome of the reaction with Hendrickson's reagent depends on the absence or presence of a base (DBU), yielding either a triphenylphosphonium-substituted iminobenzoxazine or a 4-cyano-substituted Luotonin A derivative.

Original languageEnglish
Pages (from-to)3231-3239
Number of pages9
JournalTetrahedron
Volume73
Issue number23
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Regioselectivity
Esters
Derivatives
Aminobenzoates
Benzoxazines
Anilides
Quinazolinones
Benzocaine
Nitriles
Cycloaddition
Cycloaddition Reaction
Condensation
luotonin A

Keywords

  • Cycloaddition
  • Hendrickson's reagent
  • Luotonin A
  • Weinreb amidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Remarkable regioselectivities in the course of the synthesis of two new Luotonin A derivatives. / Atia, Mohamed; Bogdán, Dóra; Brügger, Maryam; Haider, Norbert; Mátyus, P.

In: Tetrahedron, Vol. 73, No. 23, 01.01.2017, p. 3231-3239.

Research output: Contribution to journalArticle

Atia, Mohamed ; Bogdán, Dóra ; Brügger, Maryam ; Haider, Norbert ; Mátyus, P. / Remarkable regioselectivities in the course of the synthesis of two new Luotonin A derivatives. In: Tetrahedron. 2017 ; Vol. 73, No. 23. pp. 3231-3239.
@article{aeb3f38ff1c8444d9a5a87d2e03a4947,
title = "Remarkable regioselectivities in the course of the synthesis of two new Luotonin A derivatives",
abstract = "Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate reacts selectively with trimethylaluminium-activated 2-amino- or 4-aminobenzoic acid ethyl esters to give the corresponding anilides without self-condensation of the aminobenzoate building blocks. After propargylation, the quinazolinones were treated with Hendrickson's reagent, but only the para-substituted ester was found to undergo the expected [4 + 2] cycloaddition reaction, affording a new Luotonin A derivative. A different regioselectivity was observed with the ortho-substituted ester which affords a benzoxazinone under identical conditions. When the ester group in the ortho-substituted intermediate is replaced with a nitrile function, the outcome of the reaction with Hendrickson's reagent depends on the absence or presence of a base (DBU), yielding either a triphenylphosphonium-substituted iminobenzoxazine or a 4-cyano-substituted Luotonin A derivative.",
keywords = "Cycloaddition, Hendrickson's reagent, Luotonin A, Weinreb amidation",
author = "Mohamed Atia and D{\'o}ra Bogd{\'a}n and Maryam Br{\"u}gger and Norbert Haider and P. M{\'a}tyus",
year = "2017",
month = "1",
day = "1",
doi = "10.1016/j.tet.2017.04.052",
language = "English",
volume = "73",
pages = "3231--3239",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "23",

}

TY - JOUR

T1 - Remarkable regioselectivities in the course of the synthesis of two new Luotonin A derivatives

AU - Atia, Mohamed

AU - Bogdán, Dóra

AU - Brügger, Maryam

AU - Haider, Norbert

AU - Mátyus, P.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate reacts selectively with trimethylaluminium-activated 2-amino- or 4-aminobenzoic acid ethyl esters to give the corresponding anilides without self-condensation of the aminobenzoate building blocks. After propargylation, the quinazolinones were treated with Hendrickson's reagent, but only the para-substituted ester was found to undergo the expected [4 + 2] cycloaddition reaction, affording a new Luotonin A derivative. A different regioselectivity was observed with the ortho-substituted ester which affords a benzoxazinone under identical conditions. When the ester group in the ortho-substituted intermediate is replaced with a nitrile function, the outcome of the reaction with Hendrickson's reagent depends on the absence or presence of a base (DBU), yielding either a triphenylphosphonium-substituted iminobenzoxazine or a 4-cyano-substituted Luotonin A derivative.

AB - Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylate reacts selectively with trimethylaluminium-activated 2-amino- or 4-aminobenzoic acid ethyl esters to give the corresponding anilides without self-condensation of the aminobenzoate building blocks. After propargylation, the quinazolinones were treated with Hendrickson's reagent, but only the para-substituted ester was found to undergo the expected [4 + 2] cycloaddition reaction, affording a new Luotonin A derivative. A different regioselectivity was observed with the ortho-substituted ester which affords a benzoxazinone under identical conditions. When the ester group in the ortho-substituted intermediate is replaced with a nitrile function, the outcome of the reaction with Hendrickson's reagent depends on the absence or presence of a base (DBU), yielding either a triphenylphosphonium-substituted iminobenzoxazine or a 4-cyano-substituted Luotonin A derivative.

KW - Cycloaddition

KW - Hendrickson's reagent

KW - Luotonin A

KW - Weinreb amidation

UR - http://www.scopus.com/inward/record.url?scp=85018271934&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85018271934&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.04.052

DO - 10.1016/j.tet.2017.04.052

M3 - Article

AN - SCOPUS:85018271934

VL - 73

SP - 3231

EP - 3239

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 23

ER -