3192-06-1

Basic information

• Product Name: 1H-2,1-Benzothiazine, 3,4-dihydro-, 2,2-dioxide
• Synonyms: 3.4-Dihydro-1H-2.1-benzothiazin-2.2-dioxid;3,4-dihydro-2,1-benzothiazine 2,2-dioxide;3.4-Dihydro-benzo[2.1]thiazin-2.2-dioxid;3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide;3,4-Dihydro-sulfostyril
• CAS NO: 3192-06-1
• Molecular Formula: C8H9NO2S
• Molecular Weight: 183.231
• Mol File: 3192-06-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1H-2,1-Benzothiazine, 3,4-dihydro-, 2,2-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-2,1-Benzothiazine, 3,4-dihydro-, 2,2-dioxide(3192-06-1)
• EPA Substance Registry System: 1H-2,1-Benzothiazine, 3,4-dihydro-, 2,2-dioxide(3192-06-1)

Safety Data

• Hazardous Substances Data: 3192-06-1(Hazardous Substances Data)

Upstream product

• 629-59-4 tetradecane 
• 54664-50-5 β-phenethylsulfonyl azide 
• 110-82-7 cyclohexane 
• 103-63-9 1-phenyl-2-bromoethane 
• 35065-97-5 S-2-phenylethyl thioacetate 
• 4025-71-2 2-phenylethylsulfonyl chloride 
• 143769-63-5 N-benzyl 2-phenylethanesulfonamide 
• 1035670-14-4 1-benzyl-1H-2,1-benzothiazine 2,2-dioxide 
• 94532-99-7 N-(2-formylphenyl)methanesulfonamide 
• 347839-76-3 N-(2-(hydroxymethyl)phenyl)methanesulfonamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 1033628-74-8 1-(4-methoxybenzyl)-1H-benzo[c][1,2]thiazine 2,2-dioxide 
• 3192-05-0 1H-benzo[c][1,2]thiazine 2,2-dioxide 
• 71-43-2 benzene 

Downstream Products

• 3279-84-3 1-phenyl-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide 
• 120-72-9 indole 
• 496-15-1 1-indoline 

Relevant articles and documents

Towards Uniform Iodine Catalysis: Intramolecular C?H Amination of Arenes under Visible Light

A photochemical catalytic amination of arenes is presented. The reaction proceeds under benign iodine catalysis in the presence of visible light as the initiator and provides access to a range of differently substituted arylamines. A total of 29 examples demonstrate the broad applicability of this mild oxidation method. The scope of the reaction could further be expanded to silyl-tethered derivatives, which undergo intramolecular amination upon formation of seven-membered heterocycles. Cleavage of the silicon tether provides access to the corresponding 3-substituted anilines.

Oxidative fluorination of N-arylsulfonamides

We report a late stage oxidative nucleophilic fluorination of N-arylsulfonamides, a class of compounds so far not considered as precursors to 4-fluorophenyl sulfonamides. By installing a para-positioned tert-butyl substituent on the aniline, oxidative fluorination takes place regioselectively in the presence of HF·pyridine and PIDA. This methodology has been shown to give good yields for a variety of ortho- and meta-functionalised N-arylsulfonamides and has been adapted for radiofluorination to give 4-[18F]fluorophenyl sulfonamides under carrier added conditions.

Carbazole-Containing Sulfonamides as Cryptochrome Modulators

The subject matter herein is directed to carbazole-containing sulfonamide derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, B, C, D, E, F, G, H, a, and b are accordingly described. Also provided are pharmaceutical compositions comprising the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, obesity, metabolic syndrome, Cushing's syndrome, and glaucoma.

Ion-supported PhI-catalyzed cyclization of N-methoxy-2-arylethanesulfonamides with mCPBA

The ion-supported PhI-catalyzed cyclization of N-methoxy-2-arylethanesulfonamides with mCPBA was carried out to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in moderate to good yields in 2,2,2-trifluoroethanol. Here, reactive hypervalent iodine compounds, that is, ion-supported [(hydroxy)(tosyloxy)iodo]benzenes, were formed in situ and reacted with N-methoxy-2-arylethanesulfonamides to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in an electrophilic manner on the aromatic ring. Moreover, ion-supported PhI could be efficiently reused to provide the products in good yields. The same ion-supported PhI-catalyzed cyclization of N-methoxy-3-phenylpropionamide and N-methoxy-4-phenylbutyramide with mCPBA was carried out to form the corresponding N-methoxy benzolactams in moderate yields in 2,2,2-trifluoroethanol.

Facile preparation of 3,4-dihydro-2,1-benzothiazine 2,2-dioxides and related reaction with 1,3-diiodo-5,5-dimethylhydantoin under photochemical conditions

3,4-Dihydro-2,1-benzothiazine 2,2-dioxides were easily obtained in good yields by the reaction of N-methyl 2-arylethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp. When N-benzyl 2-phenylethanesulfonamide

CYCLIC SULFONAMIDE DERIVATIVES AND METHODS OF THEIR USE

The present invention is directed to cyclic sulfonamide derivatives of formula (I): or a pharmaceutically acceptable salt thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevent

Iodobenzene-catalyzed preparation of 3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides from 2-aryl-N-methoxyethanesulfonamides with m-chloroperoxybenzoic acid

Iodobenzene-catalyzed cyclization of 2-aryl-N-meth-oxyethanesulfonamides with m-chloroperoxybenzoic acid results in the corresponding 1-methoxy-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxides in moderate to good yields. In this reaction, reactive hypervalent iodine [(hydroxy)(tosyloxy)iodo] benzene, formed in situ, reacts with the 2-aryl-N-methoxyethanesulfonamides in an electrophilic manner at the aromatic ring to give the corresponding 1-methoxy-3,4-dihydro-1H-2,1 -benzothiazine 2,2-dioxides. Georg Thieme Verlag Stuttgart.

Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes

Cyclization of sulfonamides bearing an aromatic ring at the β-position with various organohypervalent iodine compounds was carried out to form the corresponding 2,1-benzothiazine derivatives. Among them, the cyclization effectively proceeded with [hydroxy

The Decomposition of β-Phenethylsulfonyl Azides. Solution Chemistry and Flash Vacuum Pyrolysis

The intramolecular cyclization of the parent title compound and a number of para-substituted derivatives (1) in solution was found to take place in low yield and to be accompanied by products of intermolecular reactions, namely, C-H insertion (4) and hydrogen abstraction (3).The use of an excess of a relatively inert solvent Freon 113 led to a better yield of the desired 3,4-dihydro-2,1-benzothiazine 2,2-dioxides (2).Flash vacuum pyrolysis (FVP) of 1 at 250-300 deg C also gave some 2, but the use of higher temperatures led to the formation of styrenes (8), indolines (9), indoles (10), sulfur dioxide, and the remarkable transformation products, the 4-substituted 6,7-dihydro-5H-1-pyrindines (7), in good yield.The styrenes result from the elimination of HN3 and SO2 from the azides, and indolines are formed in good yield by FVP of 2 at 650 deg C.The dihydropyrindines are not obtained from 2, and β-phenethynitrene is not a source of any of the above observed products.A mechanism is proposed for the formation of 7 from β-arylethylsulfonylnitrenes.Consistent with the mechanism is the observation that both 1- and 2-phenylpropanesulfonyl azide give a mixture of 6- and 7-methyl-6,7-dihydro-5H-1-pyrindines in the same ratio on FVP at 650 deg C.Thermolysis of 1a in benzene at 100 deg C gives an N-sulfonylazepine derivative.The FVP of 1 and 2 at 650 deg C are preparative routes to 7 and 9, respectively.