84512-72-1Relevant academic research and scientific papers
Rhodium-Catalyzed Annulative Coupling of Isothiazoles with Alkynes through N-S Bond Cleavage
Mihara, Gen,Noguchi, Teppei,Nishii, Yuji,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 661 - 665 (2020/01/31)
A Rh(III)-catalyzed annulative coupling of 3,5-diarylisothiazoles and alkynes is reported. The N-S bond in the isothiazole ring acts as an internal oxidant to regenerate the Rh(III) species in combination with an external Cu(II) oxidant, and the corresponding 1:2 coupling products are obtained. The remarkable difference in the reaction outcome between isothiazoles and the relevant isoxazoles has been investigated by DFT calculations, revealing that the relative stability of the enolate intermediates dictates the product selectivity.
A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles
Dwivedi, Vikas,Rajesh, Manda,Kumar, Ravi,Kant, Ruchir,Sridhar Reddy, Maddi
supporting information, p. 11060 - 11063 (2017/10/13)
A regio- and stereoselective thiocyanate addition to ynones is achieved using KSCN in AcOH at 70 °C. The reaction is extendable to ynals, ynesulfones, ynoic acids and ynoates. Adducts from ynones were readily transformed into thiazine-2-thione derivatives under slightly modified reaction conditions. In contrast, thiocyanated adducts from ynamides underwent an in situ decyanative amido cyclization towards isothiazolones. None of these events needed any transition metal or catalyst, attaining a high synthetic value.
Novel Synthesis of Di-imines by the Transformation of 1-Aryl-4,6-disubstituted Pyrimidin-2(1H)-ones
Nishio, Takehiko,Omote, Yoshimori
, p. 2149 - 2152 (2007/10/02)
The di-imines (4), which are versatile starting materials for the synthesis of heterocycles, are obtained in fair yields when the 1-aryl-4,6-disubstituted pyrimidin-2(1H)-ones (3) are treated with alkoxide, both photochemically and thermally.The di-imines (4) thus obtained, when treated with disulphide, give the 1,3-thiazine-2-thiones (8) and/or the 1-arylpyrimidine-2(1H)-thiones (9).
