Literature DB >> 31408069

Triflic anhydride mediated synthesis of 3,4-dihydroquinazolines: a three-component one-pot tandem procedure.

Christina L Magyar1, Tyler J Wall, Steven B Davies, Molly V Campbell, Haven A Barna, Sydney R Smith, Christopher J Savich, R Adam Mosey.   

Abstract

A one-pot three-component tandem reaction involving a key Pictet-Spengler-like annulation step has been developed, providing an efficient method for the synthesis of 3,4-dihydroquinazolines in moderate to good yields from amides, aldehydes, and amines. The multicomponent triflic anhydride mediated reaction tolerates the installation of numerous functional groups, affording extensive diversity about the heterocyclic scaffold.

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Year:  2019        PMID： 31408069      PMCID： PMC6767623          DOI： 10.1039/c9ob01596e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  44 in total

1.  Intermolecular Dehydrative [4 + 2] Aza-Annulation of N-Arylamides with Alkenes: A Direct and Divergent Entrance to Aza-Heterocycles.

Authors:  Ying-Hong Huang; Shu-Ren Wang; Dong-Ping Wu; Pei-Qiang Huang
Journal:  Org Lett       Date:  2019-02-26       Impact factor: 6.005

2.  Growth inhibition of human cancer cells in vitro by T-type calcium channel blockers.

Authors:  Jae Yeol Lee; Seong Jun Park; Sung Jun Park; Min Joo Lee; Hyewhon Rhim; Seon Hee Seo; Ki-Sun Kim
Journal:  Bioorg Med Chem Lett       Date:  2006-07-28       Impact factor: 2.823

3.  In vitro evaluation of the activities of the novel anticytomegalovirus compound AIC246 (letermovir) against herpesviruses and other human pathogenic viruses.

Authors:  Manfred Marschall; Thomas Stamminger; Andreas Urban; Steffen Wildum; Helga Ruebsamen-Schaeff; Holger Zimmermann; Peter Lischka
Journal:  Antimicrob Agents Chemother       Date:  2011-11-21       Impact factor: 5.191

4.  Asymmetric hydrogenation of quinazolinium salts catalysed by halide-bridged dinuclear iridium complexes bearing chiral diphosphine ligands.

Authors:  Yusuke Kita; Kosuke Higashida; Kenta Yamaji; Atsuhiro Iimuro; Kazushi Mashima
Journal:  Chem Commun (Camb)       Date:  2015-03-14       Impact factor: 6.222

5.  In vivo evaluation of oral anti-tumoral effect of 3,4-dihydroquinazoline derivative on solid tumor.

Authors:  Han Byul Kang; Hong-Kun Rim; Jin Yeong Park; Heung Woo Choi; Doo Li Choi; Ji-Hyung Seo; Kyung-Sook Chung; Geun Huh; Jungahn Kim; Dong Joon Choo; Kyung-Tae Lee; Jae Yeol Lee
Journal:  Bioorg Med Chem Lett       Date:  2011-11-28       Impact factor: 2.823

6.  Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines.

Authors:  J A Grosso; D E Nichols; M B Nichols; G K Yim
Journal:  J Med Chem       Date:  1980-11       Impact factor: 7.446

7.  Structure-based design, synthesis, and biological evaluation of dihydroquinazoline-derived potent β-secretase inhibitors.

Authors:  Arun K Ghosh; Satyendra Pandey; Sudhakar Gangarajula; Sarang Kulkarni; Xiaoming Xu; Kalapala Venkateswara Rao; Xiangping Huang; Jordan Tang
Journal:  Bioorg Med Chem Lett       Date:  2012-07-20       Impact factor: 2.823

8.  Synthesis of Functionalized Quinolines through a Reaction of Amides and Alkynes Promoted by Triflic Anhydride/Pyridine.

Authors:  Lian-Hua Li; Zhi-Jie Niu; Yong-Min Liang
Journal:  Chemistry       Date:  2017-10-12       Impact factor: 5.236

9.  2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character.

Authors:  Małgorzata Dukat; Katie Alix; Jessica Worsham; Shailesh Khatri; Marvin K Schulte
Journal:  Bioorg Med Chem Lett       Date:  2013-08-24       Impact factor: 2.823

10.  Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L.

Authors:  Wei Liu; Yongli Wang; Dan-dan He; Shu-ping Li; Yu-dan Zhu; Bo Jiang; Xue-mei Cheng; Zheng--tao Wang; Chang-hong Wang
Journal:  Phytomedicine       Date:  2015-08-28       Impact factor: 5.340
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  3 in total

1.  Dihydroquinazolines enhance 20S proteasome activity and induce degradation of α-synuclein, an intrinsically disordered protein associated with neurodegeneration.

Authors:  Taylor J Fiolek; Christina L Magyar; Tyler J Wall; Steven B Davies; Molly V Campbell; Christopher J Savich; Jetze J Tepe; R Adam Mosey
Journal:  Bioorg Med Chem Lett       Date:  2021-01-27       Impact factor: 2.823

2.  Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.

Authors:  Mario Leypold; Kyan A D'Angelo; Mohammad Movassaghi
Journal:  Org Lett       Date:  2020-10-13       Impact factor: 6.005

Review 3.  Advances in Proteasome Enhancement by Small Molecules.

Authors:  Dare E George; Jetze J Tepe
Journal:  Biomolecules       Date:  2021-11-30
  3 in total

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