- Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation
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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.
- Xu, Zhou,Li, Ke,Zhai, Rongliang,Liang, Ting,Gui, Xiaodie,Zhang, Rongli
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p. 51972 - 51977
(2017/11/22)
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- Synergistic promoting effect of ball milling and KF-alumina support for the green synthesis of benzothiazinones
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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.
- Sharifi, Ali,Ansari, Mohammad,Darabi, Hossein Reza,Abaee, M. Saeed
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p. 529 - 532
(2016/01/20)
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- Facile synthesis of 1,4-benzothiazin-3-ones from Cu-catalyzed coupling of 2-iodoanilines and 2-mercaptoacetate
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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.
- Huang, Wei-Sheng,Xu, Rongsong,Dodd, Rory,Shakespeare, William C.
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p. 5214 - 5216
(2013/09/02)
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- [NO3], a green and base-free medium for one-pot synthesis of benzothiazinones at room temperature
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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.
- Sharifi, Ali,Abaee, M. Saeed,Rouzgard, Mahdiyeh,Mirzaei, Mojtaba
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p. 2079 - 2089
(2013/06/26)
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- EP2/4 AGONISTS
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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).
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Page/Page column 36-37
(2010/11/03)
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- Regioselective one pot synthesis of 2-alkyl/aryl-4H-benzo[1,4]thiazine-3- one via microwave irradiation
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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.
- Kamila, Sukanta,Koh, Benjamin,Khan, Omair,Zhang, Hongming,Biehl, Edward R.
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p. 1641 - 1646
(2007/10/03)
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- Synthesis of some new tricyclic 1,4-benzothiazinones
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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).
- Deshmukh,Patil,Mulik
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p. 472 - 474
(2007/10/03)
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- Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide
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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.
- Zhong, Weihui,Zhang, Yongmin
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p. 3125 - 3127
(2007/10/03)
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- On the reaction of chloroalkylbenzothiazoles with alkaloides
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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.
- Florio, Saverio,Capriati, Vito,Colli, Gennara
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p. 5839 - 5846
(2007/10/03)
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- Synthesis and Antimicrobial Activity of Some 2-Alkyl-2H-1,4-benzothiazin-3(4H)-ones and 2-Alkylbenzoimidazolo-thiazolidin-3-ones
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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.
- Koos, M.
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p. 1011 - 1016
(2007/10/02)
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- Studies on the Chemistry of O,N- and S,N-Containing Heterocycles, 13. - Investigations on the Ring Contraction of 1,5-Benzothiazepines to 1,4-Benzothiazines
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Reaction of the (3R)-1,5-benzothiazepinon derivative 5 with NaNO2 in glacial acetic acid leads to the rac-1,4-benzothiazinone derivatives 6a and 7.Furthermore, reaction of 5 with NaNO2 in sulphuric acid/KBr yields the ring-contracted compound rac-6b.Compo
- Erker, Thomas,Bartsch, Herbert
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p. 403 - 406
(2007/10/02)
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- Heterocyclic aldose reductase inhibitors and methods of using them
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The invention relates to new compounds of the formula: STR1 Aldose reductase inhibitors. Treatment of certain complications of diabetes.
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- SINTESI ED ATTIVITA ANTIINFIAMMATORIA DI ALCUNI DERIVATI 1,4-BENZOTIAZINICI
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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.
- Trapani, G.,Reho, A.,Morlacchi, F.,Latrofa, A.,Marchini, P.,et al.
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p. 369 - 376
(2007/10/02)
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- 2-(Arylthio)ethanamines and &α-(Arylthio)propionamides with Antidepressant Activity
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Reaction of aziridine with thiophenols affords 2-arylthioethanamines; with 2-methylaziridine, ring opening occurs regiospecifically to provide 1-arylthio-2-propanamines.The structure of one member of this group, 1-(4-chlorophenylthio)-2-propanamine (7), has been proved by other unambiguous syntheses. 7 and isomer 12 arise from the alkylation of 4-chlorothiophenol with 2-chloropropylamine as well as from the displacement of the tosyl group in 1-(4-chlorophenylthio)-2-tosyloxypropane (13).Alkylation of 4-chlorothiophenol with α-chloropropionamide affords 11 which leads to 12 on LAH reduction.Ethanamines and propanamines are converted into guanidines, amides, ureas and thioureas.Many arylthioethanamines, e.g. 7, 22, 28, 38 and 39 (as HCl salts) and α-arylthiopropionamides, e.g. 11, 86, 91, 93 and 96 exhibit good activity in the DOPA potentiation and reserpine antagonism tests.Among these, 7 HCl is the most potent and does not inhibit rat brain MAO activity.In clinical trials, C 2998-Go compares favourably with imipramine.
- Nair, M. D.,David, J.,Nagarajan, K.
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p. 940 - 947
(2007/10/02)
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- Non-stereospecific Ring Expansion Reactions of Benzothiazoline Sulfoxides
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The stereochemistry of novel ring expansion of benzothiazoline sulfoxides to benzothiazines by reaction with acetic anhydride was examined.Reaction of trans-3-acetyl-2-ethyl-2-methylbenzothiazoline 1-oxide with acetic anhydride afforded 4-acetyl-3-ethylid
- Shimizu, Hiroshi,Ueda, Norihiro,Kataoka, Tadashi,Hori, Mikio
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p. 2571 - 2590
(2007/10/02)
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- Eliminative Ring Fission of 4-Acyl-2,3-dihydro-4H-1,4-benzothiazines
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The behavior of 4-acyl-2,3-dihydro-1,4-benzothiazines 1-11 upon treatment with lithium diisopropylamide (LDA) in THF at -78 deg C has been examined.Very marked differences have been observed.Whereas unsubstituted and monosubstituted derivatives (1-4) read
- Babudri, F.,Florio, S.,Indelicati, G.,Trapani, G.
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p. 4082 - 4087
(2007/10/02)
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