Transition metal-catalyzed C-H functionalization of arylacetic acids for the synthesis of benzothiadiazine 1,1-dioxides

被引：14

作者：

Patil, Bhausaheb N. ^{[1
]}

Lade, Jatin J. ^{[1
]}

Karpe, Aniket S. ^{[1
]}

Pownthurai, B. ^{[1
]}

Vadagaonkar, Kamlesh S. ^{[2
]}

Mohanasrinivasan, V. ^{[3
]}

Chaskar, Atul C. ^{[1
]}

机构：

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

[2] Inst Chem Technol, Dept Dyestuff Technol, Mumbai 400019, Maharashtra, India

[3] Vellore Inst Technol, Dept Biomed Sci, Vellore 632014, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 13期

关键词：

Arylacetic acids; Benzothiadiazine 1,1-dioxides; C-H functionalization; Transition metal-catalyzed; ONE-POT; 2H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES; REGIOSELECTIVE SYNTHESIS; BOND FUNCTIONALIZATIONS; PHENYLACETIC ACIDS; 1,2,4-BENZOTHIADIAZINE; 2-AMINOBENZENESULFONAMIDE; QUINAZOLINONES; CYCLOTHIAZIDE; DERIVATIVES;

D O I：

10.1016/j.tetlet.2019.02.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-catalyzed practical route for the synthesis of benzothiadiazine 1,1-dioxides has been developed. The method involves C-H functionalization of arylacetic acids to form aromatic aldehydes and their subsequent condensation with 2-aminobenzenesulfonamide. This functional group tolerant approach furnished benzothiadiazine 1,1-dioxide derivatives in good to excellent yields. Broad substrate scope, inexpensive catalyst and high product yields are notable features of this protocol. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：891 / 894

页数：4

共 50 条

[41] Synthesis and Selective Functionalization of Thiadiazine 1,1-Dioxides with Efficacy in a Model of Huntington's Disease
Terrab, Leila
Rosenker, Christopher J.
Johnstone, Lisa
Ngo, Linh K.
Zhang, Li
Ware, Nathaniel F.
Miller, Bettina
Topacio, Andrea Z.
Sannino, Sara
Brodsky, Jeffrey L.
Wipf, Peter
[J]. ACS MEDICINAL CHEMISTRY LETTERS, 2020, 11 (05): : 984 - 990
[42] Pd-Catalyzed C-H Activation: Expanding the Portfolio of Metal-Catalyzed Functionalization of Unreactive C-H Bonds by Arene-Chromium π-Complexation
Hu, Feng
Szostak, Michal
[J]. CHEMCATCHEM, 2015, 7 (07) : 1061 - 1063
[43] An Efficient Synthesis of Pyrrolo[1,2-a]quinoxalines by CopperCatalyzed C-H Activation of Arylacetic Acids
Lade, Jatin J.
Patil, Bhausaheb N.
Vhatkar, Mahendra V.
Vadagaonkar, Kamlesh S.
Chaskar, Atul C.
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) : 1579 - 1583
[44] The Use of Ammonia as an Ultimate Amino Source in the Transition Metal-Catalyzed C-H Amination
Kim, Hyunwoo
Chang, Sukbok
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (03) : 482 - 486
[45] Transition metal-catalyzed C-H Alkylations as versatile tools for synthetic transformations: a review
Tabassum, Shaheera
Zahoor, Ameer Fawad
Ali, Kulsoom Ghulam
Irfan, Muhammad
Hussain, Syed Makhdoom
Akhtar, Rabia
[J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2022, 19 (08) : 3285 - 3315
[46] Transition Metal-Catalyzed Directing-Group-Assisted C-H Activation of Phenols
Xu, Xing
Luo, Junfei
[J]. CHEMSUSCHEM, 2019, 12 (20) : 4601 - 4616
[47] Transition metal-catalyzed C-H Alkylations as versatile tools for synthetic transformations: a review
Shaheera Tabassum
Ameer Fawad Zahoor
Kulsoom Ghulam Ali
Muhammad Irfan
Syed Makhdoom Hussain
Rabia Akhtar
[J]. Journal of the Iranian Chemical Society, 2022, 19 : 3285 - 3315
[48] Biomass-Derived Solvents for Sustainable Transition Metal-Catalyzed C-H Activation
Gandeepan, Parthasarathy
Kaplaneris, Nikolaos
Santoro, Stefano
Vaccaro, Luigi
Ackermann, Lutz
[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (09) : 8023 - 8040
[49] Progress in the Transition Metal-Catalyzed C(sp2)-H Bond Functionalization of Azoarenes
Huang, Fangsheng
Chen, Xun
Xie, Ying
Zeng, Wei
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (01) : 31 - 39
[50] Transition Metal-Catalyzed Directed C(sp3)-H Functionalization of Saturated Heterocycles
Antermite, Daniele
Bull, James A.
[J]. SYNTHESIS-STUTTGART, 2019, 51 (17): : 3171 - 3204

← 1 2 3 4 5 →