Literature DB >> 21469687

Amino acids as the nitrogen-containing motifs in copper-catalyzed domino synthesis of N-heterocycles.

Wei Xu1, Hua Fu.   

Abstract

A copper-catalyzed domino method for synthesis of quinazolinones has been developed using readily available α-amino acids as the nitrogen-containing motifs. The domino process underwent Ullmann-type N-arylation, decarboxylation, aerobic oxidation, and intramolecular addition. This method should provide a new and useful strategy for construction of N-heterocycles.

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Year:  2011        PMID: 21469687     DOI: 10.1021/jo2002227

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


  9 in total

1.  Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors:  Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2013-10-06       Impact factor: 3.157

2.  Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Authors:  Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

Review 3.  Synthesis of N-Heterocycles via Oxidant-Free Dehydrocyclization of Alcohols Using Heterogeneous Catalysts.

Authors:  Kangkang Sun; Hongbin Shan; Guo-Ping Lu; Chun Cai; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-03       Impact factor: 16.823

4.  "On-Water" Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile.

Authors:  Zibin Liu; Li-Yan Zeng; Chao Li; Fubiao Yang; Fensheng Qiu; Shuwen Liu; Baomin Xi
Journal:  Molecules       Date:  2018-09-12       Impact factor: 4.411

Review 5.  Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview.

Authors:  Leyla Mohammadkhani; Majid M Heravi
Journal:  Front Chem       Date:  2020-11-16       Impact factor: 5.221

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.  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

8.  Electrochemical synthesis of quinazolinone via I2-catalyzed tandem oxidation in aqueous solution.

Authors:  Huiqing Hou; Xinhua Ma; Yingying Lin; Jin Lin; Weiming Sun; Lei Wang; Xiuzhi Xu; Fang Ke
Journal:  RSC Adv       Date:  2021-05-17       Impact factor: 4.036

9.  Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.

Authors:  YoungKu Kang; Daniel Seidel
Journal:  Org Lett       Date:  2016-08-10       Impact factor: 6.005

  9 in total

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