35529-46-5Relevant academic research and scientific papers
Transition Metal-Free Synthesis of Substituted Isothiazoles via Three-Component Annulation of Alkynones, Xanthate and NH4I
Li, Jian,Li, Jiaming,Ji, Xiaoliang,Liu, Qiang,Chen, Lu,Huang, Yubing,Li, Yibiao
, p. 1059 - 1068 (2020/12/15)
A protocol was described to access diverse isothiazoles with functionalization potential via transition metal-free three-component annulation of alkynones, potassium ethylxanthate (EtOCS2K) and ammonium iodide (NH4I). A sequential regioselective hydroamination/thiocarbonylation/intramolecular cyclization cascade achieved the efficient formation of consecutive C?N, C?S and N?S bonds in a one-pot process. (Figure presented.).
Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles
Seo, Boram,Kim, Ya Gob,Lee, Phil Ho
supporting information, p. 5050 - 5053 (2016/10/14)
A synthetic method for obtaining a wide variety of isothiazoles by the Rh-catalyzed transannulation of 1,2,3-thiadiazoles with alkyl, aryl, and heteroaryl nitriles, which proceeds via an α-thiavinyl Rh-carbenoid intermediate, was developed. The results suggest that during its reaction with nitriles, the α-thiavinyl carbene acts as an umpolung 1,3-dipole equivalent, in contrast to its behavior during its reaction with alkynes. The developed method was successfully employed to synthesize pentaoligomeric arylene compounds consisting of three benzene and two isothiazole rings.
3,4,5-Triarylisothiazoles via C-C coupling chemistry
Christoforou, Irene C.,Koutentis, Panayiotis A.
, p. 1381 - 1390 (2008/01/03)
The regiocontrolled preparation of triarylisothiazoles is presented. 3-Halo-5-phenylisothiazole-4-carbonitriles, 1 (hal = Cl) and 18 (hal = I), are converted into the corresponding 4-bromo derivatives 5 (3-hal = Cl) and 24 (3-hal = I) via a Hunsdiecker strategy while the 4-iodo analogues 7 (3-hal = Cl) and 22 (3-hal = I) are prepared via a Hoffmann and Sandmeyer strategy. Regioselective Suzuki, Stille and Negishi reactions occur at C-4 with both the 4-bromo- and 4-iodoisothiazoles 5 and 7, the latter being more reactive than the former. 3-Iodoisothiazoles 22 and 24 fail to give regiocontrolled Suzuki, Stille or Negishi couplings, however, 4-bromo-3-iodo-5-phenylisothiazole 24 gives the regiospecific palladium catalysed Ullmann-type reaction product 3,3′-bi(4-bromo-5-phenylisothiazole) 25. Alkali hydrolysis of 3-chloro-4,5-diphenylisothiazole 8 gives the 3-hydroxy analogue 12 which is converted into 3-bromo-4,5-diphenylisothiazole 13 with POBr3. 3-Bromoisothiazole 13 reacts with phenylzinc chloride to give 3,4,5-triphenylisothiazole 17 but fails to undergo effective Suzuki or Stille couplings. 3,5-Diphenylisothiazole-4-carbonitrile 26 is converted into the 4-bromo- and 4-iodo-3,5-diphenylisothiazoles 30 and 34 both of which are effective for Suzuki and Stille couplings. A series of triarylisothiazoles are prepared in this manner and fully characterised. This journal is The Royal Society of Chemistry.
Cyclic meso-ionic heterocycles. Part 24. The reaction of 1,2-dithiolium-4-olates with aniline. The formationof 11-phenylbenz[b]indeno[2,1-e]-1,4-thiazine
Newton, Christopher G.,Ollis, W. David,Rowson, Graham P.,Hamor, Margaret J.,Hamor, Thomas A.
, p. 8127 - 8142 (2007/10/02)
Reaction of the type B meso-ionic heterocycle 3,5-diphenyl-1,2-dithiolium-4-olate (1) with aniline yields N-phenyl-(3-phenyl-1-phenylimino-inden-2-yl)-amine (10) and 11-phenylbenz[bindeno[2,1-e]-1,4-thiazine (12). Mechanistic investigations establish that
Formation of 1,4,2,5-Dithiadiazines as a Heterocyclic System by Reaction of 1,4,2-Dithiazolium Salts with Sulfenamides
Yonemoto, Katsumi,Shibuya, Isao,Honda, Kazumasa
, p. 2232 - 2234 (2007/10/02)
The first example of application of sulfenamides for ring expansion on nitrogen atom has been reported to give 1,4,2,5-dithiadiazines (3) from 1,4,2-dithiazolium salts (1).The structure of 3 was confirmed by X-ray crystallographic analysis.The similar rin
THERMOLYSIS OF 1,3-DITHIOL-2-YL AZIDES AND THERMAL PROPERTIES OF THE RESULTING 1,4,2-DITHIAZINES
Nakayama, Juzo,Sakai, Atsuhiro,Tokiyama, Akira,Hoshino, Masamatsu
, p. 3729 - 3732 (2007/10/02)
2-Substituted 1,3-dithiol-2-yl azides, on thermolysis in refluxing toluene, give 3-substituted 1,4,2-dithiazines wich thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1,3-dithiol-2-yl azides undergo both ring expansion yielding 1,4,2-dithiazines and peculiar thermal dissociation into 1,3-dithiol-2-ylidene carbenes and hydrogen azide.
