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

[31] Transition Metal-Free sp3 C-H Functionalization of Arylacetic Acids for the Synthesis of 1,3,5-Triazines
Pardeshi, Sachin D.
Sathe, Pratima A.
Pawar, Balu V.
Vadagaonkar, Kamlesh S.
Chaskar, Atul C.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (18) : 2098 - 2102
[32] 1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES .4. MITSUNOBU REACTIONS OF 3-HYDROXYALKYLAMINO-4H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES AND 3-MERCAPTOALKYLAMINO-4H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES - A CONVENIENT SYNTHESIS OF BUILT-IN GUANIDINE TRICYCLES AND DISULFIDES
CHERN, JW
SHIAU, CY
WU, YH
SYNTHESIS-STUTTGART, 1991, (02): : 159 - 161
[33] Transition metal-catalyzed site- and regio-divergent C-H bond functionalization
Ping, Lucy
Chung, Da Sol
Bouffard, Jean
Lee, Sang-gi
CHEMICAL SOCIETY REVIEWS, 2017, 46 (14) : 4299 - 4328
[34] TRANSITION-METAL COMPLEXES OF THIIREN 1,1-DIOXIDES
VISSER, JP
REINHOUD.DN
LELIVELD, CG
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (03) : 178 - &
[35] Synthesis of aryne precursors via transition metal-catalyzed C-H silylation
Devaraj, Karthik
Sollert, Carina
Gates, Paul
Pilarski, Lukasz
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[36] Metal-Catalyzed C-H Functionalization Processes with "Click"-Triazole Assistance
Guerrero, Itziar
Correa, Arkaitz
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (44) : 6034 - 6049
[37] Postassembly Modifications of Peptides via Metal-Catalyzed C-H Functionalization
Tong, Hua-Rong
Li, Bo
Li, Guoxing
He, Gang
Chen, Gong
CCS CHEMISTRY, 2021, 3 (03): : 1797 - 1820
[38] 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
[39] Experimental and theoretical studies: Selective metal-catalyzed C-H functionalization
Neufeldt, Sharon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[40] Metal-Catalyzed Oxidative C-H Bond Functionalization of 1,4-Benzoxazinones
Kumar, Shankar
Ravi, Rangnath
Sahu, Tanu
Jha, Vikesh Kumar
Baweja, Renu
Jha, Abadh Kishor
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (05)

← 1 2 3 4 5 →