86333-19-9Relevant academic research and scientific papers
Gold-Catalyzed Ring Expansion of Alkynyl Heterocycles through 1,2-Migration of an Endocyclic Carbon-Heteroatom Bond
Chen, Ming,Sun, Ning,Xu, Wei,Zhao, Jidong,Wang, Gaonan,Liu, Yuanhong
, p. 18571 - 18575 (2015)
A mild and efficient gold-catalyzed oxidative ring-expansion of a series of alkynyl heterocycles using pyridine-N-oxide as the oxidant has been developed, which affords highly valuable six- or seven-membered heterocycles with wide functional group toleration. The reaction consists of a regioselective oxidation and a chemoselective migration of an endocyclic carbon-heteroatom bond (favored over C-H migration) with the order of migratory aptitude for carbon-heteroatom bonds being C-S>C-N>C-O. In the absence of an oxidant, polycyclic products are readily constructed through a ring-expansion/Nazarov cyclization reaction sequence.
SINTESI ED ATTIVITA ANTIINFIAMMATORIA DI ALCUNI DERIVATI 1,4-BENZOTIAZINICI
Trapani, G.,Reho, A.,Morlacchi, F.,Latrofa, A.,Marchini, P.,et al.
, p. 369 - 376 (2007/10/02)
A new series of dihydro-4H-1,4-benzothiazine derivatives was prepared.These compounds were obtained by reductive N-alkylation reaction with sodium borohydride in acetic acid of the corresponding 4H-1,4-benzothiazine.Some of the latter compounds were synthesized by a new synthetic method employing 2-aminobenzenethiol and alkynes as starting material. - Preliminary pharmacological data on the antiinflammatory activity of these compounds by using carrageenin paw edema assay are reported.
Reaction between 2,2'-Dithiodianiline and Activated Alkynes. Synthesis of 4H-1,4-Benzothiazines
Liso, Gaetano,Trapani, Giuseppe,Reho, Antonia,Latrofa, Andrea,Loiodice, Fulvio
, p. 567 - 572 (2007/10/02)
By the title reaction acetylenic esters (2a-c), ketones (2d-g), and the nitrile (2h) gave in all cases the corresponding 4H-1,4-benzothiazines (3) together with other products whose nature depends on the alkyne used.Thus benzothiazoline and/or benzothiazole, benzothiazepine, and vinylsulphides were obtained in the representative cases (2c, f, h) studied in detail.Some of these latter compounds have been independently synthesised by reaction of 2-aminobenzenethiol with corresponding alkyne (2).In particular conditions by the reactions between 2,2'-dithiodianiline (1) and alkynes (2f, d) we isolated bisenamine compounds (19) and (20) respectively and their intermediacy in formation of the corresponding benzothiazines (3f) and (3d) was achieved.The mechanisms of the observed reactions are also suggested.
