Base-mediated chalcogenoaminative annulation of 2-alkynylanilines for direct access to 3-sulfenyl/selenyl-1H-indoles?
Organic & Biomolecular Chemistry Pub Date: 2023-03-15 DOI: 10.1039/D3OB00279A
Abstract
An efficient and transition metal-free synthesis of 3-sulfenyl/selenyl-1H-indoles via a base-assisted chalcogenoaminative annulation of 2-alkynyl aniline with disulfides/diselenides is described. A series of 2-alkynylanilines were found compatible with dichalcogenides in this transformation providing 3-sulfenyl/selenyl-1H-indoles in good to excellent yields. The presented methodology has the advantages of easily available raw materials, functional group tolerance, and a wide range of substrates that provide access to 3-sulfenylindoles and 3-selenylindoles.
Recommended Literature
- [1] Aluminium alkyl and aryloxide complexes of pyrazine and bipyridines: synthesis and structure? Doug Ogrin,Laura H. van Poppel,Simon G. Bott,Andrew R. BarronDalton Trans., 2004, 3689-3694 10.1039/B410662H
- [2] An aptasensor for the detection of ampicillin in milk using a personal glucose meter Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu ZhangAnal. Methods, 2020,12, 3376-3381 10.1039/D0AY00256A
- [3] An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin? José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-RíosOrg. Biomol. Chem., 2012,10, 7562-7565 10.1039/C2OB25913C
- [4] An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS? Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” KimLab Chip, 2006,6, 1213-1219 10.1039/B601954D
- [5] An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon SongPhys. Chem. Chem. Phys., 2014,16, 5295-5300 10.1039/C3CP54624A
- [6] Aggregation-induced chiral symmetry breaking of a naphthalimide–cyanostilbene dyad? Xin Li,Liangliang Zhu,Sai Duan,Yanli Zhao,Hans ?grenPhys. Chem. Chem. Phys., 2014,16, 23854-23860 10.1039/C4CP04070H
- [7] Acenaphthenic hopanoids, a novel series of aromatised Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre AlbrechtChem. Commun., 2001, 1976-1977 10.1039/B105198A
- [8] An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes? Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce YeAnalyst, 2021,146, 5542-5549 10.1039/D1AN01071A
- [9] Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties Huabin Zhang,Shaowu DuCrystEngComm, 2014,16, 4059-4068 10.1039/C3CE42419G
- [10] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4