Ag-Catalyzed Remote Dehydrogenative-coupling of Unactivated C(sp3)-H Alcohols with Quinazolines for the Synthesis of δ-Hydroxylalkyl Substituted Quinazolines in Aqueous Media

被引：4
作者：
Xie, Dayu [1 ]
Liu, Yan [1 ]
Liu, Xixian [1 ]
Yang, Qin [1 ]
Peng, Yiyuan [1 ]
机构：
[1] Jiangxi Normal Univ China, Coll Chem & Chem Engn, Key Lab Green Chem Jiangxi Prov, Nanchang, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Quinazoline; delta-hydroxylalkyl substituted quinazoline; 1,5-HAT reaction; Minisci-type reaction; silver catalysis; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; 2-SUBSTITUTED QUINAZOLINES; OXIDATIVE ANNULATION; REGIOSELECTIVE HETEROARYLATION; BOND FUNCTIONALIZATION; HYDROGEN-ATOM; ACID; DERIVATIVES; ACTIVATION;
D O I：
10.1002/ejoc.202300993
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient silver-catalyzed delta-regioselective unactivated C(sp(3) )-H of free alcohols dehydrogenative coupling with quinazolines for the synthesis of delta-hydroxylalkyl substituted quinazolines in aqueous media has been developed. Various alcohols including 1 degrees and 2 degrees alcohols, reacted with quinazolines through 1,5-hydrogen-atom transfer strategies to give the corresponding 2- or 4- delta-hydroxylalkyl substituted quinazolines with good to excellent yields under mild reaction conditions. Notably, several substituted quinazolines and quinazolinones could be selectively dehydrogenative-coupled with divergent free alcohols. This protocol provides a platform to access divergent functionalizations of quinazolines and quinazolinones to meet the growing needs for screening.
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页数：8
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  • [1] Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines
    Arachchige, Pandula T. Kirinde
    Yi, Chae S.
    [J]. ORGANIC LETTERS, 2019, 21 (09) : 3337 - 3341
  • [2] Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids
    Auti, Prashant S.
    George, Ginson
    Paul, Atish T.
    [J]. RSC ADVANCES, 2020, 10 (68) : 41353 - 41392
  • [3] Remote C(sp3)-H Arylation and Vinylation of N-Alkoxypyridinium Salts to δ-Aryl and δ-Vinyl Alcohols
    Bao, Xu
    Wang, Qian
    Zhu, Jieping
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (50) : 11630 - 11634
  • [4] Dual Photoredox/Copper Catalysis for the Remote C(sp3)-H Functionalization of Alcohols and Alkyl Halides by N-Alkoxypyridinium Salts
    Bao, Xu
    Wang, Qian
    Zhu, Jieping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 2139 - 2143
  • [5] An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
    Bhat, Subrahmanya Ishwar
    Das, U. K.
    Trivedi, Darshak R.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (04) : 1253 - 1259
  • [6] Bond dissociation energies of organic molecules
    Blanksby, SJ
    Ellison, GB
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 255 - 263
  • [7] 2,4-DIAMINO-6,7-DIMETHOXYQUINAZOLINES .1. 2-[4-(1,4-BENZODIOXAN-2-YLCARBONYL)PIPERAZIN-1-YL] DERIVATIVES AS ALPHA-1-ADRENOCEPTOR ANTAGONISTS AND ANTIHYPERTENSIVE AGENTS
    CAMPBELL, SF
    DAVEY, MJ
    HARDSTONE, JD
    LEWIS, BN
    PALMER, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) : 49 - 57
  • [8] sp3 C-H oxidation by remote H-radical shift with oxygen- and nitrogen-radicals: a recent update
    Chiba, Shunsuke
    Chen, Hui
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (24) : 4051 - 4060
  • [9] Synthesis of quinazolinones and quinazolines
    Connolly, DJ
    Cusack, D
    O'Sullivan, TP
    Guiry, PJ
    [J]. TETRAHEDRON, 2005, 61 (43) : 10153 - 10202
  • [10] Palladium-Catalyzed Minisci Reaction with Simple Alcohols
    Correia, Camille A.
    Yang, Luo
    Li, Chao-Jun
    [J]. ORGANIC LETTERS, 2011, 13 (17) : 4581 - 4583
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