Iron-catalyzed Csp3-Csp3 bond formation via dehydrative cross coupling reaction: Facile access to new hybrid dihydroquinazolines having quinoline, isoquinoline, quinoxaline and azoles

被引：8

作者：

Srinivasulu, A. ^{[1
,2
]}

Shantharjun, B. ^{[1
,2
]}

Kumar, R. Arun ^{[1
]}

Reddy, K. Rajender ^{[1
,2
]}

机构：

[1] CSIR, Inorgan & Phys Chem Div, Indian Inst Chem Technol, Hyderabad 500007, Telangana State, India

[2] Acad Sci & Innovat Res, New Delhi 110025, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 15期

关键词：

Cross coupling; Dehydrative; Iron catalyst; Quinazoline; AZAARENES NUCLEOPHILIC-ADDITION; C-H FUNCTIONALIZATION; N-SULFONYL ALDIMINES; TRANSITION-METAL; PROPARGYLIC ALCOHOLS; METHYL AZAARENES; ACID; ALKYLATION; DERIVATIVES; DISCOVERY;

D O I：

10.1016/j.tetlet.2017.03.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple, efficient and straight forward approach was developed for the synthesis of new hybrid nitrogen heterocycles bearing dihydroquinazoline with quinoline, isoquinoline, quinoxaline and azole via iron-catalyzed dehydrative cross coupling reaction between heterocyclic aminol and 2-methyl azaarenes. Furthermore, this protocol applied to couple simple methyl ketones to achieve C4-alkylated-dihydroquinazolines with broad substrate scope. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1501 / 1506

页数：6

共 10 条

[1] Iron-catalyzed C-C bond formation via cross dehydrative coupling reaction of N-heterocyclic aminols with electron rich arenes: facile access to C4-aryl-dihydroquinazolines
Kumar, R. Arun
Srinivasulu, A.
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TETRAHEDRON, 2016, 72 (06) : 794 - 802
[2] Iron-Catalyzed Csp2-Csp3 Cross-Coupling via Double Decarboxylation: One Step Synthesis of Remote Polar Alkenes
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[3] Csp3-PIII Bond Formation via Cross-Coupling of Umpolung Carbonyls with Phosphine Halides Catalyzed by Nickel
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[4] C-N and C-P bond formation via cross dehydrative coupling reaction: an efficient synthesis of novel 3,4-dihydroquinazolines
Saidulu, G.
Kumar, R. Arun
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RSC ADVANCES, 2014, 4 (99): : 55884 - 55888
[5] Iron-catalyzed C-N bond formation via oxidative Csp3-H bond functionalization adjacent to nitrogen in amides and anilines: Synthesis of N-alkyl and N-benzyl azoles
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TETRAHEDRON LETTERS, 2015, 56 (28) : 4200 - 4203
[6] Iron-catalyzed cascade reaction of C(sp3)-Se bond cross-coupling/C-N bond formation
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CHEMICAL COMMUNICATIONS, 2021, 57 (44) : 5426 - 5429
[7] Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3-H bond activation using a new metal-organic framework as catalyst
To, Tuong A.
Vo, Yen H.
Nguyen, Hue T. T.
Ha, Phuong T. M.
Doan, Son H.
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[8] Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes
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[9] Bu4NI Catalyzed C-N Bond Formation via Cross-Dehydrogenative Coupling of Aryl Ethers (Csp3-H) and Tetrazoles (N-H)
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ORGANIC LETTERS, 2015, 17 (22) : 5586 - 5589
[10] n-Bu4NI/TBHP-catalyzed C-N bond formation via cross-dehydrogenative coupling of 1H-1,2,4-triazoles (N-H) and methylarenes (Csp3-H)
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RSC ADVANCES, 2016, 6 (85): : 82289 - 82293

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