Generation of (2-oxoindolin-3-yl)methanesulfonohydrazides via a photo-induced reaction of N-(2-iodoaryl)acrylamide, DABSO, and hydrazine
Literature Information
Publication Date
2016-05-13
DOI
10.1039/C6QO00163G
Impact Factor
5.281
Authors
Kaida Zhou, Hongguang Xia
View Original
Abstract
A photo-induced catalyst-free three-component reaction of N-(2-iodoaryl)acrylamide, sulfur dioxide, and hydrazine is reported. Under ultraviolet irradiation, diverse (2-oxoindolin-3-yl)methanesulfonohydrazides are generated in moderate to good yields. During the process, the sulfonyl group can be easily incorporated via insertion of sulfur dioxide in the absence of any metals or photo-redox catalysts under mild conditions. A plausible mechanism is proposed, which involves 5-exo radical cyclization and subsequent insertion of sulfur dioxide.
Recommended Journals
Journal of Chemical Sciences
Bioorganic & Medicinal Chemistry Letters
Herald of the Russian Academy of Sciences
Chinese Journal of Chemistry
Medicinal Chemistry Research
Polycyclic Aromatic Compounds
Journal of the Indian Institute of Science
Acta Metallurgica Sinica-English Letters
Critical Reviews in Solid State and Materials Sciences
Heteroatom Chemistry
Related Literature
Azaborahelicene fluorophores derived from four-coordinate N,C-boron chelates: synthesis, photophysical and chiroptical properties
José Francisco Rizo, Jesús F. Arteaga, Ludovic Favereau, Abel Ros, Uwe Pischel
2023-12-19
Research Article
DOI: 10.1039/D3QO01762A
Correction: An efficient metal free synthesis of 2-aminobenzothiozoles – a greener approach
Ganesh Sambasivam, Govindarajulu Gavara, Ramraj S, Gaikwad Rajendra, Karthikeyan Sivashanmugam
2023-11-02
Correction
DOI: 10.1039/D3OB90143B
Directing-group-free strategy for the iodine-mediated regioselective dichalcogenation of indolines: understanding the full catalytic cycles
Xiaoxiang Zhang, Chenrui Liu, Wenwei Pang, Xiaoting Gu, Wanxing Wei, Zhuan Zhang, Haiyan Chen, Taoyuan Liang
2023-12-11
Research Article
DOI: 10.1039/D3QO01492D
Asymmetric permanganate dihydroxylation of enoates: substrate scope, mechanistic insights and application in bicalutamide synthesis
Peilong Gu, Shuangshuang Wang, Xiangxiang Wen, Jinxin Tian, Chao Wang, Lili Zong, Choon-Hong Tan
2023-12-11
Research Article
DOI: 10.1039/D3QO01729J
Visible light as a sole requirement for alkylation of α-C(sp3)–H of N-aryltetrahydroisoquinolines with alkylboronic acids
Feihu Cong, Wenjing Zhang, Gan Zhang, Jie Liu, Yicheng Zhang, Chao Zhou
2023-10-15
Paper
DOI: 10.1039/D3OB01154B
Syntheses of 3H-1,2,4-triazol-3-ones by copper-promoted oxidative N–N bond formation of amidines with isocyanates
Baihui Liang, Xiangya Cai, JingYu Liu, Jie Huang, Youzhi Chen, Haiyin Deng, Quanquan Zhou, Tianxiang Chen, Xiuwen Chen, Zhongzhi Zhu
2023-11-21
Research Article
DOI: 10.1039/D3QO01565C
Enantio- and diastereoselective conjugate addition of pyridyl alkyl ketones to enones by Cu(ii)-Lewis acid/Brønsted base catalysis
Soojin Kwak, Minhyeok Lee, Eunji Sim, Sarah Yunmi Lee
2023-12-06
Research Article
DOI: 10.1039/D3QO01707A
Hydantoin hexameric rosettes: harnessing H-bonds for supergelation and liquid crystals
Lucía González, Iván Marín, Rosa M. Tejedor, Joaquín Barberá, Pilar Romero, Alberto Concellón, Santiago Uriel, José L. Serrano
2023-12-04
Research Article
DOI: 10.1039/D3QO01832F
Porphyrin- and Bodipy-helicene conjugates: syntheses, separation of enantiomers and chiroptical properties
Vincent Silber, Marion Jean, Nicolas Vanthuyne, Natalia Del Rio, Paola Matozzo, Jeanne Crassous, Romain Ruppert
2023-10-25
Paper
DOI: 10.1039/D3OB01459B
You might also like
Compound Q&A
How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?
2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...
615-45-22-Methylbenzene-1,4-...
Compound Q&A
Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...
132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
871826-15-2(6-Chloropyridazin-3...
Compound Q&A
What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?
2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...
77772-72-62-Fluoro-3-methylphe...
Compound Q&A
What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?
When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...
177476-75-43-Methoxy-4-nitroben...
Compound Q&A
What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?
When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...
211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
90347-86-74-Ethynylbenzamide
Compound Q&A
What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?
3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...
186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A
What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?
(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...
500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A
What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?
Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...
102196-18-92-[4-(Hydroxymethyl)...
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure](https://static.chemtradehub.com/structs/209/2093416-31-8-3162.webp "4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure")
4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
2093416-31-8
Molecular Formula:
C21H28N4O7
![4-Chloro-2-{[(2-chlorophenoxy)acetyl]amino}benzoic acid structure](https://static.chemtradehub.com/structs/351/351424-20-9-9467.webp "4-Chloro-2-{[(2-chlorophenoxy)acetyl]amino}benzoic acid structure")
4-Chloro-2-{[(2-chlorophenoxy)acetyl]amino}benzoic acid
CAS Number:
351424-20-9
Molecular Formula:
C15H11Cl2NO4
N-(4-Chlorobenzyl)-beta-alanine hydrochloride (1:1)
CAS Number:
1172479-10-5
Molecular Formula:
C10H13Cl2NO2
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.