Literature DB >> 22852777

Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: a strategy to construct quinazolinones.

Hidemasa Hikawa1, Yukari Ino, Hideharu Suzuki, Yuusaku Yokoyama.   

Abstract

A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η(3)-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.

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Year:  2012        PMID： 22852777     DOI： 10.1021/jo301282n

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


  10 in total

1.  Sunflower-Assisted Bio-Derived ZnO-NPs as an Efficient Nanocatalyst for the Synthesis of Novel Quinazolines with Highly Antioxidant Activities.

Authors:  Mahesh S; Boya Palajonnala Narasaiah; Himabindu B; Balaji G L; Jangampalli Adi Pradeepkiran; Harihara Padhy
Journal:  Antioxidants (Basel)       Date:  2022-03-31

2.  Photoinduced Enhanced Decomposition of TBHP: A Convenient and Greener Pathway for Aqueous Domino Synthesis of Quinazolinones and Quinoxalines.

Authors:  Daisy Sarma; Biju Majumdar; Barsha Deori; Siddarth Jain; Tridib K Sarma
Journal:  ACS Omega       Date:  2021-04-29

Review 3.  Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis.

Authors:  Rosa Ortiz; Raquel P Herrera
Journal:  Molecules       Date:  2017-04-01       Impact factor: 4.411

4.  Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters.

Authors:  Joshua T Gavin; Joel K Annor-Gyamfi; Richard A Bunce
Journal:  Molecules       Date:  2018-11-09       Impact factor: 4.411

5.  Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones from o-nitrobenzamide and alcohols.

Authors:  Ke Wang; Hao Chen; Xinyan Dai; Xupeng Huang; Zhiqiang Feng
Journal:  RSC Adv       Date:  2021-04-07       Impact factor: 3.361

6.  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

7.  Straightforward synthesis of quinazolin-4(3H)-ones via visible light-induced condensation cyclization.

Authors:  Wuji Sun; Xue Ma; Yuqi Pang; Lifeng Zhao; Qidi Zhong; Chunyan Liu; Qiangwen Fan
Journal:  RSC Adv       Date:  2022-01-07       Impact factor: 3.361

8.  β-Cyclodextrin: a supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one.

Authors:  Bijeta Mitra; Gyan Chandra Pariyar; Pranab Ghosh
Journal:  RSC Adv       Date:  2021-01-05       Impact factor: 3.361

9.  Electro-oxidative cyclization: access to quinazolinones via K2S2O8 without transition metal catalyst and base.

Authors:  Yongzhi Hu; Huiqing Hou; Ling Yu; Sunying Zhou; Xianghua Wu; Weiming Sun; Fang Ke
Journal:  RSC Adv       Date:  2021-09-24       Impact factor: 4.036

10.  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
  10 in total

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