I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization

被引：65

作者：

Vadagaonkar, Kamlesh S. ^{[1
]}

Kalmode, Hanuman P. ^{[1
]}

Murugan, Kaliyappan ^{[2
]}

Chaskar, Atul C. ^{[1
,3
]}

机构：

[1] Inst Chem Technol, Dept Dyestuff Technol, Bombay 400019, Maharashtra, India

[2] Natl Taiwan Univ, Taipei 10617, Taiwan

[3] Univ Mumbai, Natl Ctr Nanosci & Nanotechnol, Mumbai 400098, Maharashtra, India

来源：

RSC ADVANCES | 2015年 / 5卷 / 08期

关键词：

ONE-POT SYNTHESIS; ALPHA-HYDROXY KETONES; SOLID-PHASE SYNTHESIS; O-PHENYLENEDIAMINES; OXIDATION PROCESSES; BIOLOGICAL-ACTIVITY; EFFICIENT CATALYST; AEROBIC OXIDATION; HIGHLY EFFICIENT; DERIVATIVES;

D O I：

10.1039/c4ra08589b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One-pot, atom-economic synthesis of quinoxalines has been achieved through generation of arylglyoxal from easily available ethylarenes, ethylenearenes and ethynearenes, and subsequent condensation with o-phenylenediamines. Catalytic I-2 with TBHP as an oxidant in DMSO is the system of choice for this domino reaction involving C-H functionalization/oxidative cyclization. This metal-free, mechanistically distinct and functional group tolerant tandem approach could be a powerful complement to traditional approaches for the synthesis of quinoxalines.

引用

页码：5580 / 5590

页数：11

共 50 条

[41] Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant
Wang, Dong-Hui
Wasa, Masayuki
Giri, Ramesh
Yu, Jin-Quan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) : 7190 - +
[42] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups
Rouquet, Guy
Chatani, Naoto
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11726 - 11743
[43] sp3 C-H and sp2 C-H agostic ruthenium complexes:: a combined experimental and theoretical study
van der Boom, ME
Iron, MA
Atasoylu, O
Shimon, LJW
Rozenberg, H
Ben-David, Y
Konstantinovski, L
Martin, JML
Milstein, D
INORGANICA CHIMICA ACTA, 2004, 357 (06) : 1854 - 1864
[44] Copper-Catalyzed C(sp2)-C(sp2) Bond Formation via Single C(sp2)-H Activation
Parmar, Himanshu V.
Adodariya, Yash J.
Patel, Unnati P.
Shrivastav, Pranav S.
Maru, Jayesh J.
CHEMISTRYSELECT, 2024, 9 (02):
[45] Metal-catalyzed functionalization of sp3 C-H bond
Yun, Sang Young
Wang, Kung-Pern
Mamidipalli, Phani
Lee, Nam-Kyu
Lee, Daesung
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[46] Metal-free in situ sp3, sp2, and sp C-H functionalization and oxidative cross coupling with benzamidines hydrochloride: a promising approach for the synthesis of α-ketoimides
Kalmode, Hanuman P.
Vadagaonkar, Kamlesh S.
Chaskar, Atul C.
RSC ADVANCES, 2014, 4 (104) : 60316 - 60326
[47] A Simple and Efficient Approach to the Synthesis of 2-Phenylquinazolines via sp3 C-H Functionalization
Zhang, Jintang
Zhu, Dapeng
Yu, Chenmin
Wan, Changfeng
Wang, Zhiyong
ORGANIC LETTERS, 2010, 12 (12) : 2841 - 2843
[48] Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
Richers, Johannes
Heilmann, Michael
Drees, Markus
Tiefenbacher, Konrad
ORGANIC LETTERS, 2016, 18 (24) : 6472 - 6475
[49] CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds
Li, ZP
Li, CJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) : 6968 - 6969
[50] CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds
1600, American Chemical Society, Columbus, United States (127):

← 1 2 3 4 5 →