Copper-Catalyzed Cascade Syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and Quinoxalin-2(1H)-ones through Capturing S and N Atom Respectively from AcSH and TsNH2

被引：72

作者：

Chen, Dingben ^{[1
,2
]}

Wang, Zhi-Jing ^{[1
]}

Bao, Weiliang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

[2] Taizhou Univ, Coll Pharmaceut & Chem Engn, Linhai 317000, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 16期

基金：

高等学校博士学科点专项科研基金;

关键词：

ALDOSE REDUCTASE INHIBITOR; ONE-POT SYNTHESIS; QUINOXALINONE DERIVATIVES; COUPLING REACTIONS; PHASE SYNTHESIS; EFFICIENT; 1,4-BENZOTHIAZINE; CYCLIZATION; AGENTS;

D O I：

10.1021/jo101253a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH2 via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.

引用

页码：5768 / 5771

页数：4

共 50 条

[21] Iron-Catalyzed Direct C3-H Trifluoromethylthiolation of Quinoxalin-2(1H)-ones
Chen, Xiaoyu
Geng, Yang
Zhu, Yu
Zou, Dapeng
Wu, Yangjie
Wu, Yusheng
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (02) : 214 - 219
[22] Copper-Catalyzed Direct C-3 Benzylation of Quinoxalin-2(1H)-ones with Methylarenes under Microwave Irradiation
Hu, Leqian
Yuan, Jinwei
Fu, Junhao
Zhang, Taotao
Gao, Lele
Xiao, Yongmei
Mao, Pu
Qu, Lingbo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4113 - 4120
[23] Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones
Peng, Sha
Liu, Jiao
Yang, Li-Hua
Xie, Long-Yong
MOLECULES, 2022, 27 (15):
[24] Microwave-assisted one-pot synthesis of benzo[b][1,4]thiazin-3(4H)-ones via Smiles rearrangement
Zuo, Hua
Li, Zhu-Bo
Ren, Fang-Kui
Falck, J. R.
Lijuan, Meng
Ahn, Chuljin
Shin, Dong-Soo
TETRAHEDRON, 2008, 64 (41) : 9669 - 9674
[25] Crystal structure of (E)-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)-methyl]-2H-benzo[b][1,4] thiazin-3(4H)-one
Sebbar, Nada Kheira
Ellouz, Mohamed
Essassi, El Mokhtar
Saadi, Mohamed
El Ammari, Lahccn
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O423 - U396
[26] Green and efficient synthesis of 1,2-bis(2H-benzo[e][1,3]oxazin-3(4H)-yl)ethanes and 1,2-bis(2H-benzo[e][1,3]thiazin-3(4H)-yl)ethanes
Nongkhlaw, R. L.
Nongrum, R.
Tumtin, S.
Phucho, I. T.
ARKIVOC, 2019, : 255 - 264
[27] Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Halo-Substituted Quinolin-2(1H)-ones, Coumarins, Quinoxalin-2(1H)-ones, and Chromenes
Thi Thanh Huyen Luong
Brachet, Etienne
Brion, Jean-Daniel
Messaoudi, Samir
Alami, Mouad
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) : 1771 - 1780
[28] Regioselective syntheses of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones from arylglycidates when exposed to 1,2-diaminobenzenes
Mamedov, Vakhid A.
Mamedova, Vera L.
Syakaev, Victor V.
Voronina, Julia K.
Mahrous, Essam M.
Korshin, Dmitry E.
Latypov, Shamil K.
Sinyashin, Oleg G.
TETRAHEDRON, 2020, 76 (41)
[29] Visible-light-promoted direct C-H/S-H cross-coupling of quinoxalin-2(1H)-ones with thiols leading to 3-sulfenylated quinoxalin-2(1H)-ones in air
Xie, Long-Yong
Chen, Yan-Ling
Qin, Li
Wen, Yuan
Xie, Jian-Wei
Tan, Jia-Xi
Huang, Ying
Cao, Zhong
He, Wei-Min
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (24) : 3950 - 3955
[30] One-Pot Synthesis of Benzo[1,4]thiazin-3(4H)-ones and a Theoretical Study of the S-N Type Smiles Rearrangement Mechanism
Zhao, Yongmei
Wu, Yanmiao
Jia, Jiong
Zhang, Dongju
Ma, Chen
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19): : 8501 - 8506

← 1 2 3 4 5 →