Benzothiazoles. V

Mizuno, Yoshihisa; Adachi, Kikuo

doi:10.1248/yakushi1947.72.6_745

Cited by 12 publications

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“…Thus the direct nitration of 2-methylbenzothiazole gives 2-methyl-6-nitrobenzothiazole (1). 9 As the preparation of 5-nitroderivatives by direct nitration of 2 with the Fe/HCl under sonochemical conditions 12 followed by the reaction with acetic anhydride provides corresponding acetylaminoderivatives 3 and 4 (Scheme 1). …”

Section: Resultsmentioning

confidence: 99%

Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring

Sigmundová¹,

Zahradnı́k²,

Magdolen³

et al. 2008

Arkivoc

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New 2-styryl benzothiazolium salts substituted on the heterocyclic ring have been synthesised by the condensation of 3-alkyl-2-methylbenzothiazolium halides with 4-substituted benzaldehydes. The intramolecular charge transfer from the electron-donor substituent to the benzothiazolium ring is a typical feature of the prepared compounds. This type of benzothiazolium derivatives can be used as pharmaceutical substances as well as compounds with nonlinear optical response. Antimicrobial in vitro activity was determined and the influence of substituents has been evaluated. The substituents on the heterocyclic ring in positions 5 and 6 do not increase the biological activity significantly.

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Section: Resultsmentioning

confidence: 99%

Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring

Sigmundová¹,

Zahradnı́k²,

Magdolen³

et al. 2008

Arkivoc

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“…2-Methyl-6-nitrobenzothiazole was obtained from nitration of 2-methylbenzothiazole by described methods [13]. 2-Methyl-6-nitrobenzothiazole was obtained from nitration of 2-methylbenzothiazole by described methods [13].…”

Section: Methodsmentioning

confidence: 99%

Preliminary studies on the use of cyanines as ligands in dye‐affinity chromatography of proteins

Pardal¹,

Nunes²,

Gama³

et al. 2002

Coloration Technology

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An isothiocyanato-functionalised cyanine was synthesised, characterised, immobilised on agarose gel and the dye-affinity adsorbent ability for purifying some standard proteins (e.g. bovine serum albumin, trypsin and chymotrypsin) was analysed. The influence of mobile phase composition on the chromatographic behaviour of these proteins was also studied. A selective interaction between the studied proteins and the immobilised cyanine was obtained.

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“…Analytical data are given in table IV. a) Dye 12 (table I) 7.6 g of 2,3-dimethyl-7-methanesulfonamidobenzothiazolium methylsulfate, 7.6 ml of ethyl orthoformate and 50 ml of acetic anhydride are refluxed for 20 minutes.…”

Section: Dyesmentioning

confidence: 99%

“…req. : N YO,14.4; S %, 16.5; %, 23,7; found: N YO, 14.4; S %, 16.5; -NO, %, 23.6.Reduction of 2-methyl-7-nirrobenzorhiazole a) With tin-hydrochloric acid 5.5 g of 2-methyl-7-nitrobenzothiazole were reduced according to[6], yielding 1.3 g of a product m.p. *120".…”

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confidence: 99%

The Isomeric Sulfo‐2‐Methylbenzothiazoles and their Use in the Synthesis of Sensitising Polymethine Dyes

Libeer

Depoorter

Nys

1971

Bulletin des Soc Chimique

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Les 4-, 5-, 6-et 7-amino-2-metliylbe1izothiazoles (1) furent transformes en sulfochlorures correspondants 2. Par hydrolyse ceux-ci fournissent les acides sulfoniques 3 et par arnmonolyse les sulfonamides 4 (SchCma I). Un mode de preparation d u 2-m6thyl-7-nitrobenzothiazole ne laissant plus aucun doute quant a la structure du produit obtenu fut elabore (Schema VI). Enfin, les auteurs decrivent la synthbse d e colorants polymethiniques en partant des bases mentionntes et de plusieurs d e leurs derives et Btudient I'effet des substituants sur les proprietes optiques.The isomeric 4-, 5-, 6-and 7-amino-2-metliylbenzothiazoles (1) were converted into the corresponding sulfochlorides 2, which afforded the sulfonic acids 3 on hydrolysis and the sulfonamides 4 on ammonolysis (Chart I). An unequivocal synthesis of 2-methyl-7-nitrobenzothiazole has been elaborated (Chart VI). The heterocyclic bases mentioned and some derivatives were used in the synthesis of spectral sensitizing dyes. The influence of the substituents on the spectral properties of the dyes is investigated.Carbocyanines containing a benzothiazole nucleus substituted a t the 6-position with a sulfo or a sulfamyl group have been reported by Kiprianov and Ushenko [2].The benzothiazoles required as intermediates were obtained by chlorosulfonating 2-methylbenzothiazole and treating the sulfochloride 2 with water or ammonia (Chart 11). On repeating their experiments we obtained in fact a sulfochloride with the m.p. (68") reported. However, in contradiction with the statements of Kiprianov and Ushenko, this product appeared to be not homogeneous, since repeated recrystallisations from hexane raised the m.p. up to 103". Furthermore, conversion of the sulfochloride with m.p. 68" with ammonia resulted in a mixture of sulfonamides (m.p. 184", lit.[2]: I84-185"), which we were able to separate into three isomers with m.p. 214", 245" and 228" respectively. The isomer with m.p. 214" proved to be identical with the sulfonarnide obtained in the sanie way, but starting from the sulfochloride of m.p. 103".These results clearly indicate that the 2-methyl-6-chlorosulfonyl-(2c), 6-sulfo-(3c) and 6-sulfamylbenzothiazole (4c) obtained by Kiprianov and Ushenko were not free from isomers; moreover, the problem remains of determining the position of the substituents in the various isomers.In the course of an investigation of sensitising dyes bearing sulfonamido groups on different positions, we attempted to achieve the synthesis of pure 2, 3 and 4 in a * The contents ofthis paper are the subject of patent applications

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Benzothiazoles. V

Cited by 12 publications

References 0 publications

Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring

Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring

Preliminary studies on the use of cyanines as ligands in dye‐affinity chromatography of proteins

The Isomeric Sulfo‐2‐Methylbenzothiazoles and their Use in the Synthesis of Sensitising Polymethine Dyes

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