Literature DB >> 24060201

Copper-catalyzed activation of α-amino peroxy and hydroxy intermediates to iminium ion precursor: an access to C4-substituted 3,4-dihydroquinazolines via oxidative cross coupling strategy.

R Arun Kumar1, G Saidulu, Balasubramanian Sridhar, Shiuh Tzung Liu, K Rajender Reddy.   

Abstract

A simple and straightforward approach to access C4-substituted-3,4-dihydroquinazolines has been achieved, where copper-catalyzed activation of α-amino peroxide and hydroxide intermediates to iminium ion precursors has been realized as an important step. Reactions of these intermediates with alkynes, indoles, pyrrole, and silylenol ether afforded the structurally diverse C4-substituted-3,4-dihydroquinazoline derivatives in good yields.

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Year:  2013        PMID: 24060201     DOI: 10.1021/jo401622r

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


  5 in total

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

Authors:  Christina L Magyar; Tyler J Wall; Steven B Davies; Molly V Campbell; Haven A Barna; Sydney R Smith; Christopher J Savich; R Adam Mosey
Journal:  Org Biomol Chem       Date:  2019-08-28       Impact factor: 3.876

2.  Friedel-Crafts synthesis of bis(trifluoromethylated)-4-aryl-3,4-dihydroquinazolines, bis(trifluoromethylated)-3,4-dihydroquinazoline-4-ols and trifluoromethyl arylketoimines using N-aryltrifluoroacetimidoyl chlorides and benzene derivatives.

Authors:  Elham Kazemi; Ali Darehkordi; Alireza Abbasi
Journal:  Mol Divers       Date:  2021-02-03       Impact factor: 2.943

3.  Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine.

Authors:  Jimena E Díaz; Silvia Ranieri; Nadia Gruber; Liliana R Orelli
Journal:  Beilstein J Org Chem       Date:  2017-07-27       Impact factor: 2.883

4.  Synthesis of dihydroquinazolines from 2-aminobenzylamine: N 3 -aryl derivatives with electron-withdrawing groups.

Authors:  Nadia Gruber; Jimena E Díaz; Liliana R Orelli
Journal:  Beilstein J Org Chem       Date:  2018-09-26       Impact factor: 2.883

5.  New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence.

Authors:  Long Zhao; Mao-Lin Yang; Min Liu; Ming-Wu Ding
Journal:  Beilstein J Org Chem       Date:  2022-03-04       Impact factor: 2.883

  5 in total

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