Cascade syntheses of aza[2,1-b][1,3]-benzothiazinone heteropolycyclic compounds from cyclic thiourea catalyzed by Cu(I)

Domino Reactions Initiated by Copper‐Catalyzed Aryl‐I Bond Thiolation For the Switchable Synthesis of 2,3‐Dihydrobenzothiazinones and Benzoisothiazolones

“…[17] Over the past decades, several different methodologies have been devised for the synthesis of 2,3-dihydrobenzothiazinones. For example, the annulation reactions of 2-mercaptobenzoic acid with imines, [18] the annulation of thioureas with perfluorobenzoyl chlorides or methyl o-iodobenzoate, [19] the condensation of 2-mercaptobenzamides with aldehydes, [20] and the cyclization of 2-mercaptobenzamides with alkyl propiolates [21] are predominantly utilized methods. While the employment of the odour smelling thiophenol derivative or sensitive acyl chloride as substrate remains as restriction in the known approaches, developing new synthetic protocols allowing the synthesis of 2,3-dihydrobenzothiazinones without using sensitive or odour chemical is of high urgency.…”

Investigations of possible prodrug structures for 2-(2-mercaptophenyl)tetrahydropyrimidines: reductive conversion from anti-HIV agents with pyrimidobenzothiazine and isothiazolopyrimidine scaffolds

“…Spectral data were in good agreement with those previously reported. 26 Crystal structure: C 11 H 10 N 2 OS, M w : 218.27, primitive monoclinic, a = 10.7456 (6), b = 10.9466 (6), c = 16.6473(7) Å, β = 97.422(2)°, V = 1941.78(17) Å 3 , space group P2 1 /n (no. 14), Z = 8.…”

“…The extract was dried over MgSO 4 , and concentrated to give the title compound 10 as colorless crystals (5.2 mg, 27%); mp 132-134 °C (from toluene); IR (neat) ν max / cm −1 : 1662 (CvO), 1608 (CvN); δ H (500 MHz, CDCl 3 ): 1.98-2.03 (2H, m, CH 2 ), 3.57 (2H, t, J 5.7, CH 2 ), 4.02 (2H, t, J 6.0, CH 2 ), 7.17 (1H, d, J 8.0, Ar), 7.26-7.29 (1H, m, Ar), 7.47 (1H, ddd, J 1 = J 2 7.7, J 3 1.6, Ar), 8.24 (1H, dd, J 1 8.0, J 2 1. 26 Crystal structure: C 11 H 10 N 2 OS, M w : 218.27, primitive monoclinic, a = 10.7456 (6), b = 10.9466 (6), c = 16.6473(7) Å, β = 97.422(2)°, V = 1941.78(17) Å 3 , space group P2 1 /n (no. 14), Z = 8.…”

Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

“…Methyl 2-iodobenzoates 303 reacted with a wide range of cyclic thioureas 304 in a similar coppercatalyzed cyclization to give 5, 6, and 7-membered b-fused rings 305 (Scheme 92). 162…”