Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions

被引：33

作者：

Noikham, Medena ^{[1
]}

Kittikool, Tanakorn ^{[1
]}

Yotphan, Sirilata ^{[1
]}

机构：

[1] Mahidol Univ, Dept Chem, Ctr Excellence Innovat Chem PERCH CIC, Fac Sci, Rama 6 Rd, Bangkok 10400, Thailand

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 12期

关键词：

iodine; quinoxalinone; indole; oxidative coupling; metal-free; N BOND FORMATION; TYROSINE KINASE-ACTIVITY; ONE-POT SYNTHESIS; C-H; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; GROWTH-FACTOR; COPPER; INHIBITORS; PALLADIUM;

D O I：

10.1055/s-0037-1609445

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient iodine-catalyzed oxidative cross-dehydrogenative coupling reaction of quinoxalinones and indoles has been developed. Without the requirement of peroxide and acid, this reaction utilizes a catalytic amount of molecular iodine to facilitate the C-C bond formation under ambient air. This simple and easy-to-handle protocol represents an interesting synthetic alternative with a good scope and functional group compatibility.

引用

页码：2337 / 2346

页数：10

共 11 条

[1] Efficient one-step synthesis of 3-(indol-2-yl)quinoxalin-2(1H)-ones via electrochemical oxidative cross-dehydrogenative coupling
Zhang, Hao
Hu, Lishan
Yu, Kai
Lou, Lan-Lan
Liu, Shuangxi
NEW JOURNAL OF CHEMISTRY, 2022, 46 (17) : 8037 - 8042
[2] TFA/DMSO-Promoted Cross-Dehydrogenative Coupling of Hetaryl Thiols with Indoles: Access to 3-(Hetarylsulfenyl)indole under Mild Conditions
Truong, Tan Sang
Retailleau, Pascal
Nguyen, Thanh Binh
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (02)
[3] Iodine-Catalyzed Oxidative Coupling of Indolin-2-ones with Indoles: Synthesis of 3,3-Disubstituted Oxindole Compounds
Li, Ruo-Pu
Wang, Zheng-Lin
Zhang, Yun-Hao
Tan, Zhi-Yu
Xu, Da-Zhen
CHEMISTRYSELECT, 2022, 7 (28):
[4] Selective Synthesis of 2-(Indol-3-Yl)Phenols via Iodine-Catalyzed C3-Arylation of Indoles with Cyclohexanones
Yin, Qi
Zhou, Xinlin
Zhang, Chao
Chen, Shanping
Li, Yuxia
Deng, Guo-Jun
ADVANCED SYNTHESIS & CATALYSIS, 2025,
[5] An efficient synthesis of 3-(indol-3-yl)quinoxalin-2-ones with TfOH-catalyzed Friedel-Crafts type coupling reaction in air
Han, Yan-Yan
Wu, Zhi-Jun
Zhang, Xiao-Mei
Yuan, Wei-Cheng
TETRAHEDRON LETTERS, 2010, 51 (15) : 2023 - 2028
[6] Reductive acid-catalyzed rearrangement of 3-(2-nitrobenzyl)quinoxalin-2(1De)-ones in the presence of Na2S2O4 - effective method for the synthesis of 2-(indol-2-yl)benzimidazoles
Mamedov, Vakhid A.
Khafizova, Elena A.
Syakaev, Victor V.
Bazanova, Olga B.
Zamaletdinova, Anastasiya I.
Rizvanov, Il'dar Kh.
Latypov, Shamil K.
Sinyashin, Oleg G.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (09) : 1033 - 1044
[7] Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions
Alagiri, Kaliyamoorthy
Devadig, Pradeep
Prabhu, Kandikere R.
TETRAHEDRON LETTERS, 2012, 53 (12) : 1456 - 1459
[8] Direct C3 Alkoxylation of Quinoxalin-2(1H)-ones with Alcohols via Cross-Dehydrogenative Coupling under Catalyst-Free Conditions
Yang, Qiming
Han, Xulin
Zhao, Jiquan
Zhang, Hong-Yu
Zhang, Yuecheng
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) : 11417 - 11424
[9] Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles
Shelke, Ganesh M.
Kumar, Anil
SYNTHESIS-STUTTGART, 2017, 49 (18): : 4321 - 4326
[10] Iodine-catalyzed conjugate addition of indoles onto en-1,4-dione: A novel synthesis of 3-(1-(1H-indol-3-yl)-2-oxo-2-phenylethyl)indolin-2-ones as antibacterial and antifungal agents
Reddy, B. V. Subba
Rajeswari, N.
Sarangapani, M.
Reddy, G. Roopa
Madan, Ch.
Kumar, K. Pranay
Rao, M. Srinivasa
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (21) : 6510 - 6514

← 1 2 →