7028-57-1

Upstream product

• 598-72-1 2-Bromopropionic acid 
• 137-07-5 2-amino-benzenethiol 
• 535-11-5 Ethyl 2-bromopropionate 
• 4892-01-7 2-(2-nitro-phenylsulfanyl)-propionic acid 
• 139565-00-7 (+/-)-2-Brommethyl-2H-1,4-benzothiazin-3(4H)-on 
• 27816-36-0 2-Chloropropionamide 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 110704-27-3 2-(1-chloroethyl)benzothiazole 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 17147-80-7 2-(1-hydroxyethyl)-1,3-benzothiazole 
• 94590-63-3 (3R)-3-Amino-2,3-dihydro-1,5-benzothiazepin-4(5H)-on 
• 95779-64-9 (R)-3-phthalimido-2,3-dihydro-1,5(5H)-benzothiazepin-4-one 
• 100236-26-8 (2R)-3-(2-Aminophenylthio)-2-phthalimidopropionsaeure 

Downstream Products

• 93301-19-0 2,2-dimethyl-2,3-dihydro-4H-1,4-benzothiazine 
• 93301-21-4 2-benzyl-2-methyl-2,3-dihydro-4H-1,4-benzothiazine 
• 93301-25-8 4-acetyl-2-benzyl-2-methyl-2,3-dihydro-4H-1,4-benzothiazine 
• 93301-29-2 4-acetyl-2-benzyl-2-methyl-2,3-dihydro-4H-1,4-benzothiazine 1-oxide 
• 87012-09-7 N-benzoyl-N-<2-(methylthio)phenyl>propen-1-ylamine 
• 87012-00-8 4-benzoyl-2-methyl-2,3-dihydro-1,4-benzothiazine 
• 1247021-59-5 2-methyl-4-[2-(trifluoromethyl)benzyl]-2H-1,4-benzothiazin-3(4H)-one 
• 139605-59-7 5-methyl-[1,2,4]-triazino-6-oxo[3,4-c]-3(1H)-[1,4]benzothiazine 
• 58960-00-2 2-Methyl-2,3-dihydro-4H-1,4-benzothiazine 
• 90921-53-2 2,2-dimethyl-3-oxo-2,3-dihydro-4H-1,4-benzothiazine 
• 97678-16-5 erythro-3,4-dihydro-2(α-hydroxybenzyl)-4H-2-methyl-3-oxo-2H-1,4-benzothiazine 
• 97678-16-5 threo-3,4-dihydro-2(α-hydroxybenzyl)-4H-2-methyl-3-oxo-2H-1,4-benzothiazine 
• 93301-18-9 2-benzyl-2-methyl-3-oxo-2,3-dihydro-4H-1,4-benzothiazine 

Relevant academic research and scientific papers

Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation

An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.

Synergistic promoting effect of ball milling and KF-alumina support for the green synthesis of benzothiazinones

A solvent-free procedure was developed for the reaction of 2-aminothiophenols with 2-bromoalkanoates, where KF-Al2O3 support and ball milling cooperatively lead to a green and efficient synthesis of several benzothiazinone derivatives in good to excellent yields. The catalyst could be recycled in further reactions while maintaining its activity.

Facile synthesis of 1,4-benzothiazin-3-ones from Cu-catalyzed coupling of 2-iodoanilines and 2-mercaptoacetate

A novel synthesis of 1,4-benzothiazin-3-ones was developed from Cu-catalyzed coupling of readily available substituted 2-iodoanilines with 2-mercaptoacetate. The new method offers clear advantages over existing approaches for its one-step simple operation, wider reaction scope, and moderate to excellent isolated yields.

[NO3], a green and base-free medium for one-pot synthesis of benzothiazinones at room temperature

A general and efficient room-temperature procedure is developed for high-yield synthesis of 2H-benzo[b][1,4]thiazin-3(4H)-one derivatives in one pot from the reaction of 2-aminothiophenols with 2-bromoalkanoates in ionic liquid [bmim]NO3 without the use of any catalyst, base, or additive. Products were obtained in good yields by simple extraction with Et2O followed by evaporation of the volatile contents and recrystallization from Et2O. The ionic liquid was recycled and reused in the next reaction without the loss of its activity.

EP2/4 AGONISTS

EP2/4 compounds having improved dual pharmacological activity are described. The uniqueness of using EP2/4 dual agonists resides in their ability to modify both uveoscleral outflow via the ciliary muscle and conventional outflow via trabecular meshwork and Schlemm's canal all in the same treatment paradigm. The compounds can be employed for the treatment of glaucoma and ocular hypertension. Formula (I).

Regioselective one pot synthesis of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3- one via microwave irradiation

A series of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3-ones have been synthesized by microwave irradiation of ethyl-2-bromo-2-alkyl/aryl acetate and 2-amino thiophenol in the presence of 1,8-diazabicyclo-[5.4.0]undec-7-ene and N-methylpiperidine. All compounds were characterized by 1H NMR, 13C NMR and elemental analyses, and by X-ray crystallography in the case of 2-methyl-4H-benzo[1,4]thiazin-3-one.

Synthesis of some new tricyclic 1,4-benzothiazinones

2-Aminothiophenol on reaction with dimethyl oxalate and methyl 2-chloropropionate gives 1,4-benzothiazinone, (1a, 1b) which when reacted with ethyl chloroacetate give N-ethoxycarbonylmethyl-1,4-benzothiazine-2,3-dione (2a1). Compound 2 on reaction with hydrazine hydrate affords N-hydrazidomethyl-1,4-benzothiazine-2,3-dione (3). Compound 3 is cyclized in presence of ammonium acetate and acetic acid to give 5-methyl[1,2,4]triazino-6-oxo[3,4-c]-3(1H)-[1,4]benzothiazine (4b1). Compound 1 on reaction with phosphorus oxychloride gives 3-chloro-1,4-benzothiazine-3-one (5a) which when reacts with ammonium sulfocyanide affords 1,4-benzothiazin-2-one-3-ylisocyanate (6a). Compound 6 when reacted with methyl cyanide gives the desired tricyclic compound 2-thio-6-methyl[1,3,5]triazolo[3,4-c]benzothiazine-2-one (7a).

Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide

Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with α-halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions.

On the reaction of chloroalkylbenzothiazoles with alkaloides

2-chloroalkylbenzothiazoles 1a-c react with alkoxides to give substitution and ring-expanded products 3 and 4. The substitution ring-enlargement competition much depends upon the solvent, the substitution reaction being preferred in alcohols and the ring-enlargement in DMF.

Synthesis and Antimicrobial Activity of Some 2-Alkyl-2H-1,4-benzothiazin-3(4H)-ones and 2-Alkylbenzoimidazolo-thiazolidin-3-ones

Sodium 2-aminothiophenoxide (1) reacts with ethyl 2-bromoalkanoates (2) under direct cyclization to form 2-alkyl-2H-1,4-benzothiazin-3(4H)-ones (3).Reaction of the sodium salt of 2-mercaptobenzimidazole (4) with 2 or 2-bromoalkanoic acids (5) affords only S-alkylated products (6 or 7, respectively).The cyclization products - 2-alkylbenzoimidazolothiazolidin-3-ones (8) - can be obtained only from the corresponding 2-(2-benzimidazolylthio)alkanoic acids (7) by the action of acetic anhydride.Both compounds 3 and 8 exhibit only moderate antimicrobial activity against some gram-positive bacteria. - Keywords: 4H-1,4-Benzothiazines; Benzoimidazolothiazolidines; Antimicrobial activity.