80281-92-1Relevant academic research and scientific papers
Synthesis of Fused 1λ4,2-Thiazines(2-Azathiabenzenes)
Gairns, Raymond S.,Grant, Richard D.,Moody, Christopher J.,Rees, Charles W.,Tsoi, Sui Chung
, p. 483 - 490 (2007/10/02)
By analogy with the formation of acyclic sulphimides from sulphides and azides, mild thermolysis of aryl, hetaryl, and vinyl azides with a 1,6-related, conjugated thioether function gives the cyclic sulphimides, 1λ4,2-thiazines.Thus in boiling toluene the azidothiophenes (9), (12) and (18), the azidobenzenes (14), and the azidofuran (16) give the fused 1λ4,2-thiazines (10), (13), (19), (15), and (17) respectively.Yields are high when the products are stabilised by delocalisation of the ylidic (N--S+) charges, but low when they are not.The S-allyl sulphimide (10c) is not isolable however since it rearranges spontaneously to the thienopyrrole (11).In contrast with azidothiophene (12), the 'reversed' thiophenes (20) do not give the corresponding 3,4-fused thienothiazines; the nitrene from the azide (20a) cyclises preferentially to carbon to give thienopyrrole (21) and that from the azide (20b) inserts into a methyl group to give the thienopyridine (22).Preferential cyclisation onto carbon rather than sulphur is also observed in the benzene series; thus azides (24) give 4-thio substitued indole-2-carboxylates (25) in good yield.The spectroscopic properties and thermal stabilities of all the 1λ4,2-thaizines prepared show them to be pyramidal cyclic S-N ylides rather than planar aromatic systems.
Photochemical Rearrangement of Fused 1λ4,2-Thiazines (2-Azathiabenzenes); Rapid Migration of Methylthio and Phenylthio Groups
Gairns, Raymond S.,Tsoi, Siu Chung,Moody, Christopher J.,Rees, Charles W.
, p. 497 - 500 (2007/10/02)
Irradiation of fused 1λ4,2-thiazines (1) gives the isomeric fused pyrroles (2).The structures of the thienopyrroles (2a,b) are assigned by decoupling and n.O.e. experiments on the thienopyrroles (4a,b) formed from them by hydrolysis and
Synthesis and X-Ray Structure of an Azathiabenzene Derivative, a Cyclic Sulphimide
Moody, Christopher J.,Rees, Charles W.,Tsoi, Siu Chung,Williams, David J.
, p. 927 - 928 (2007/10/02)
Decomposition of azidothiophens (3) gives the thieno4,2>thiazines (4), which are stable cyclic sulphimides, the ylidic nature of 4a being confirmed by its properties and X-ray structure determination; photolysis of the sulphimides (4)
