496-30-0Relevant academic research and scientific papers
Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones
Rewcastle, Gordon W,Janosik, Tomasz,Bergman, Jan
, p. 7185 - 7189 (2001)
The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b′]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed.
Preparation of Benzothiopyrano[2,3-b]indoles by thereaction of 1,3-dihydroindole-2-thiones with certain dienophiles
Kamila, Sukanta,Biehl, Ed
, p. 2785 - 2795 (2004)
Benzothiopyrano[2,3-b]indoles were prepared by the cyclization of 1,3-dihydroindole-2-thiones with varions dienophiles. The 1,3-dihydroindole-2- thiones were readily synthesized by the reaction of oxindole with P2S5 followed by a piperidine-mediated condensation of the resulting thioindole with a suitable aromatic aldehyde.
Synthesis of thieno[2,3-b]indole-2,3-diones and their ring expansions induced by diazomethane
Berg, Robert,Bergman, Jan
, p. 5654 - 5658 (2017)
Indole-2-thione 3 reacted quickly with oxalyl chloride to yield thieno[2,3-b]indole-2,3-dione 4 together with the isomer thiazolo[3,2-a]indole-2,3-dione 5. These thieno[2,3-b]indole-2,3diones underwent ring expansions when treated with diazomethane and e.g. thieno[2,3-b]indole-2,3-dione 4 gave the thiopyrano derivative 16, after two insertions.
Synthesis of 2-(Arylthio)indolenines via Chemoselective Arylation of Thio-Oxindoles with Arynes
Saputra, Adi,Fan, Rong,Yao, Tuanli,Chen, Jian,Tan, Jiajing
supporting information, p. 2683 - 2688 (2020/05/18)
A chemoselective S-arylation reaction of thio-oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2-(arylthio)indolenines in good to excellent yields. Besides, this simple operat
Indolylthio glycosides as effective building blocks for chemical glycosylation
Demchenko, Alexei V.,Shrestha, Ganesh,Panza, Matteo,Singh, Yashapal,Rath, Nigam P.
, p. 15885 - 15894 (2021/01/19)
The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.
Nickel(ii)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles
Yang, Wei,Lin, Xiaobin,Zhang, Yongyan,Cao, Weidi,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 10002 - 10005 (2020/09/15)
A nickel(ii) catalyzed enantioselective thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles was realized with modified chiral N,N′-dioxide ligands, affording a variety of C3-substituted indole derivatives in high yields (up to 95%) with excellent enantioselectivities (up to 96% ee) under mild reaction conditions. A possible transition state model was proposed based on previous reports and the X-ray crystal structure of the catalyst.
Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2-Sulfenyl Benzimidazoles with Boronic Acids
Lopes, Alexandra Basilio,Choury, Mickael,Wagner, Patrick,Gulea, Mihaela
supporting information, p. 5943 - 5947 (2019/08/26)
A new tandem palladium-catalyzed reaction involving a Suzuki-Miyaura coupling, a desulfenylative coupling, and a hydrothiolation of a triple bond is reported. Notably, the desulfenylative coupling occurs without copper(I) assistance and the hydrothiolatio
One-pot mild and efficient synthesis of [1,3]thiazino[3,2-: A] indol-4-ones and their anti-proliferative activity
Rhodes, Steven,Short, Spencer,Sharma, Sidhika,Kaur, Ramneet,Jha, Mukund
supporting information, p. 3914 - 3920 (2019/04/30)
A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-a]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in situ, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4H-[1,3]thiazino[3,2-a]indol-4-one and 8-methyl-2-propyl-4H-[1,3]thiazino[3,2-a]indol-4-one compounds.
Metal-free hydroamination of alkynes: A mild and concise synthesis of thiazolo[3,2- a ]indoles and their cytotoxic activity
Bhave, Vishakha S.,Hojo, Ryoga,Jha, Mukund,Rhodes, Steven,Short, Spencer
supporting information, p. 4263 - 4270 (2019/11/13)
A metal-free, mild and efficient method for the synthesis of thiazolo[3,2- a ]indoles has been developed starting from indoline-2-thiones. The reaction methodology involves first the formation of thermally labile 2-(prop-2-ynylthio)-1 H -indole intermedia
A THIONATION PROCESS AND A THIONATING AGENT
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Page/Page column 9; 10, (2012/08/27)
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
