Literature DB >> 21675775

Synthesis of quinazolin-4(3H)-ones via Pd(II)-catalyzed intramolecular C(sp2)-H carboxamidation of N-arylamidines.

Bin Ma1, Yong Wang, Jiangling Peng, Qiang Zhu.   

Abstract

An efficient synthesis of quinazolin-4(3H)-ones from N-arylamidines, through palladium-catalyzed intramolecular C(sp(2))-H carboxamidation, has been developed. The reaction, carried out in the presence of 1.0 equiv of CuO as oxidant under atmospheric pressure of CO, provides diversified 2-aryl(alkyl)quinazolin-4(3H)-ones in reasonable to good yields from N-arylamidines, which are readily derived from anilines and nitriles. Compared with existing approaches to quinazolin-4(3H)-ones, the current strategy features atom-economy and step-efficiency.

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Year:  2011        PMID： 21675775     DOI： 10.1021/jo2007362

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

2.  Palladium-catalyzed N-monoarylation of amidines and a one-pot synthesis of quinazoline derivatives.

Authors:  Meredeth A McGowan; Camille Z McAvoy; Stephen L Buchwald
Journal:  Org Lett       Date:  2012-07-05       Impact factor: 6.005

3.  N-(2-Iodo-phen-yl)benzene-carbox-imid-amide.

Authors:  Yin-Jun Zhang; Dong Wang; Hai-Liang Zhang; Yu-Guang Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-17

4.  Direct palladium(II)-catalyzed synthesis of arylamidines from aryltrifluoroborates.

Authors:  Jonas Sävmarker; Jonas Rydfjord; Johan Gising; Luke R Odell; Mats Larhed
Journal:  Org Lett       Date:  2012-04-17       Impact factor: 6.005

5.  Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature.

Authors:  Jiewen Chen; En Liang; Jie Shi; Yinrong Wu; Kangmei Wen; Xingang Yao; Xiaodong Tang
Journal:  RSC Adv       Date:  2021-01-28       Impact factor: 3.361

6.  ortho-Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3H)-ones: a convergent synthetic route to bouchardatine and sildenafil.

Authors:  Kyeongha Kim; Hun Young Kim; Kyungsoo Oh
Journal:  RSC Adv       Date:  2020-08-21       Impact factor: 4.036

7.  Direct intramolecular double cross-dehydrogentive-coupling (CDC) cyclization of N-(2-pyridyl)amidines under metal-free conditions.

Authors:  Fengping Yi; Chao Fu; Qihui Sun; Huazhen Wei; Genfa Yu; Weiyin Yi
Journal:  RSC Adv       Date:  2019-12-19       Impact factor: 3.361

8.  Synthesis, antitumor activity, 3D-QSAR and molecular docking studies of new iodinated 4-(3H)-quinazolinones 3N-substituted.

Authors:  Marcia Pérez-Fehrmann; Víctor Kesternich; Arturo Puelles; Víctor Quezada; Fernanda Salazar; Philippe Christen; Jonathan Castillo; Juan Guillermo Cárcamo; Alejandro Castro-Alvarez; Ronald Nelson
Journal:  RSC Adv       Date:  2022-08-02       Impact factor: 4.036

9.  Decarboxylative palladium(II)-catalyzed synthesis of aryl amidines from aryl carboxylic acids: development and mechanistic investigation.

Authors:  Jonas Rydfjord; Fredrik Svensson; Alejandro Trejos; Per J R Sjöberg; Christian Sköld; Jonas Sävmarker; Luke R Odell; Mats Larhed
Journal:  Chemistry       Date:  2013-08-28       Impact factor: 5.236
  9 in total

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