Rh(III)-Catalyzed C-H Annulation of 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with Vinylene Carbonates

被引：0

作者：

Ittamalla, Chaitanya ^{[1
,3
]}

Chary, D. Yogananda ^{[1
,3
]}

Balasubramanian, Sridhar ^{[2
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Fluoroagrochem, Hyderabad 500007, India

[2] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, India

[3] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 04期

关键词：

3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides; C-C and C-N bond formations; ortho-C-H bond activation; transition metal catalysis; vinylene carbonate; 1,1-DIOXIDES; ACTIVATION; POTENTIATION; INHIBITORS;

D O I：

10.1002/ejoc.202300983

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method has been developed for the synthesis of fused dihydroisoquinoline frameworks through a Rh(III)-catalyzed annulation of 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with vinylene carbonates by C-H bond activation. This is the first report on the oxidative C-H functionalization of aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxide with vinylene carbonate to afford angularly fused heterocycles in good yields with high functional group tolerance. In this approach, vinylene carbonate acts as a glycolaldehyde surrogate to construct the fused dihydroisoquinoline ring systems.

引用

页数：5

共 50 条

[21] Rh(III)-Catalyzed Redox-Neutral C-H Activation/[3+2] Annulation of N-Phenoxy Amides with Propargylic Monofluoroalkynes
Zhong, Xiuhua
Lin, Shuang
Gao, Hui
Liu, Fu-Xiaomin
Zhou, Zhi
Yi, Wei
ORGANIC LETTERS, 2021, 23 (06) : 2285 - 2291
[22] Rh(III)-Catalyzed Oxidative Annulation of 2-Arylquinoxalines with Cyclic 2-Diazo-1,3-diketones by C-H Bond Activation
Ajay, Chidrawar
Chary, Devulapally Yogananda
Balasubramanian, Sridhar
Reddy, Basi Subba V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (13)
[23] Rhodium(III)-Catalyzed C-H/N-H Alkyne Annulation of Nonsymmetric 2-Aryl (Benz)imidazole Derivatives: Photophysical and Mechanistic Insights
Dias, Gleiston G.
Paz, Esther R. S.
Kadooca, Juliana Y.
Sabino, Adao A.
Cury, Luiz A.
Torikai, Kohei
de Simone, Carlos A.
Fantuzzi, Felipe
da Silva Junior, Eufranio N.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 264 - 278
[24] Rh(III)-Catalyzed Oxidative Domino C-H/N-H Annulation: Diarylureas as Arylamine Donors for the Assembly of Indolo[2,1-a]isoquinolines
Cao, Xiyang
Zhang, Zhiguo
Li, Jingya
Shi, Bingbing
Li, Mengjuan
Zhang, Guisheng
Zhang, Xingjie
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21) : 13672 - 13682
[25] Direct Synthesis of Benzo[c]carbazoles by Pd-Catalyzed C-H [4+2] Annulation of 3-Arylindoles with External 1,3-Dienes
Gerardin, Baptiste
Traboulsi, Iman
Pal, Suman
Lebunetelle, Gabrielle
Ramondenc, Yvan
Hoarau, Christophe
Schneider, Cedric
ORGANIC LETTERS, 2022, : 8164 - 8169
[26] Copper-Catalyzed Tandem Radical Cyclization of 8-Ethynyl-1-naphthyl-amines for the Synthesis of 2H-Benzo[e][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties
Chen, Xia
Zhang, Lianpeng
Wang, Yuzhe
Qiu, Guanyinsheng
Liang, Qinghui
Zhou, Hongwei
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19) : 12526 - 12534
[27] Nickel-Catalyzed Regio- and Enantioselective Annulation Reactions of 1,2,3,4-Benzothiatriazine-1,1(2H)-dioxides with Allenes
Miura, Tomoya
Yamauchi, Motoshi
Kosaka, Akira
Murakami, Masahiro
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4955 - 4957
[28] Easy synthesis of imidazo[1,5-a]indol-3-ones through Rh(iii)-catalyzed C-H allenylation/annulation
Zhu, Bin
Yao, Zhenyu
Huang, Lang
Cui, Xiuling
CHEMICAL COMMUNICATIONS, 2021, 57 (90) : 12012 - 12015
[29] Overview of the synthetic routes of 2-alkyl-4-hydroxy-2H-1, 2-benzothiazine-3-carboxamides-1,1-dioxides (oxicams) and their analogues
Gouda, Moustafa A.
SYNTHETIC COMMUNICATIONS, 2017, 47 (17) : 1527 - 1558
[30] Synthesis of benzoazepine derivatives via Rh(iii)-catalyzed inert C(sp2)-H functionalization and [4+3] annulation
Xu, Yuanshuang
Zhang, Linghua
Liu, Mengyang
Zhang, Xiaopeng
Zhang, Xinying
Fan, Xuesen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (38) : 8706 - 8710

← 1 2 3 4 5 →