cas 63837-11-6, 5-BROMO-2-METHYLBENZOTHIAZOLE

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Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
supporting information
p. 7851 - 7856
(2019/10/11)

Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides
Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.
Imazaki, Yusuke,Shirakawa, Eiji,Ueno, Ryota,Hayashi, Tamio
supporting information
p. 14760 - 14763
(2012/11/07)

Regioselective one-pot synthesis of 2-aryl-6-bromobenzothiazole from arylaldehyde and 2-aminothiophenol with phenyltrimethylammonium tribromide in the presence of a catalytic amount of antimony(III) bromide
Various 2-aryl-6-bromo-1,3-benzothiazoles were regioselectively afforded in good yields by the reaction of arylaldehydes and 2-aminothiophenol with phenyltrimethylammonium tribromide in the presence of a catalytic amount of SbBr3 in CH2Cl2 at room temperature.
Sayama, Shinsei
experimental part
p. 1267 - 1274
(2011/06/27)

An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides
A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.
Pan, Jun,Wang, Xinyan,Zhang, Yong,Buchwald, Stephen L.
supporting information; experimental part
p. 4974 - 4976
(2011/11/06)

Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides
The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in
Shen, Xiaoqiang,Hyde, Alan M.,Buchwald, Stephen L.
supporting information; experimental part
p. 14076 - 14078
(2011/01/10)

Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R14; with R1, R2, R3, R4, R5, R6, R7, R8, and R14 defined herein.
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Page/Page column 108

(2008/06/13)

Synthesis of 5- and 6-Substituted 2-Methylbenzothiazoles under Conditions of Metal Complex Catalysis
Methods are proposed for preparation of 5- and 6-substituted 2-methylbenzothiazoles by reactions of organozinc and organotin compounds with 5- and 6-bromo-2-methylbenzothiazoles, catalyzed by palladium complexes. The reactions of organozinc compounds with 5(6)-bromo-2-methylbenzothiazoles occur in THF at 20°C in the presence of PdCl2(dppf), and those of organotin compounds are carried out in DMF, aqueous DMF, or water at 40-100°C in the presence of PdCl2, Pd(OAc)2, or PdCl2(PPh3)2.
Bumagin,Nikitina,Beletskaya
p. 1803 - 1811
(2007/10/03)

Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (zopolrestat) and congeners
A new working hypothesis that there is a hitherto unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50 = 1.9 x 10-8 M) and was orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications (ED50 = 18.5 mg/kg). Optimization of this lead through medicinal chemical rationale, including analogy from other drug series, led to more potent congeners of 207 and culminated in the design of 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (216, CP-73,850, zopolrestat). Zopolrestat was found to be more potent than 207, both in vitro and in vivo. Its IC50 against AR and ED50 in the acute test were 3.1 x 10-9 M and 3.6 mg/kg, respectively. Its ED50s in reversing already elevated sorbitol accumulation in rat sciatic nerve, retina, and lens in a chronic test were 1.9, 17.6, and 18.4 mg/kg, respectively. It was well absorbed in diabetic patients, resulting in high blood level, showed a highly favorable plasma half-life (27.5 h), and is undergoing further clinical evaluation. An assortment of synthetic methods used for the construction of benzothiazoles, including an efficient synthesis of zopolrestat, is described. Structure-activity relationships in the new series are discussed.
Mylari,Larson,Beyer,Zembrowski,Aldinger,Dee,Siegel,Singleton
p. 108 - 122
(2007/10/02)

HETEROCYCLIC OXOPHTHALAZINYL ACETIC ACIDS
A heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula, wherein X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH2 or CHR5Z is vinyl; R1 is hydroxy, or a prodrug group; R2 is a heterocyclic group, R3 and R4 are hydrogen or the same or a different substituent, and R5 is hydrogen, methyl or trifluoromethyl. The pharmaceutically acceptable acid addition salts of the above compounds wherein R1 is di(C1-C4)alkylamino or (C1-C4)alkoxy substituted by N-morpholino or di(Cl-C4)alkylamino and the pharmaceutically active base addition salts of the above compounds wherein R1 is hydroxy are also aldose reductase inhibitors
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(2008/06/13)