60. The application of the Hofmann reaction to the synthesis of heterocyclic compounds. Part I. Synthesis of alloxazine from quinoxaline-2 : 3-dicarboxylic acid

Baxter, R. A.; Spring, F. S.

doi:10.1039/jr9450000229

Cited by 12 publications

(3 citation statements)

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“…The N-substituted 2-carbamoylethyldimethylsulfonium p-toluenesulfonate derivatives (2, 3, 4a-m) listed in Tables 1 and 2 were prepared by the general procedures outlined in Scheme 1. Treatment of methyl 3-(methylthio)propionate (7) with 25% aqueous NH 3 7 gave 2-carbamoylethyl methyl sulfide (8). Cyclohexylamine (9) was condensed with 3-(methylthio)propionyl chloride in the presence of triethylamine to give 2-(cyclohexylcarbamoyl)ethyl methyl sulfide (10).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfoniump-Toluenesulfonate Derivatives

et al. 1998

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The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]carbamoyl]ethyldimeth ylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfoniump-Toluenesulfonate Derivatives

et al. 1998

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“…By using other /3-keto esters and o-phenylenediamines under basic conditions, other products analogous to 2-benzimidazoleacetone (XXIV) have been obtained (662). These products are listed in Ethyl -chloroacetoacetate and o-phenylenediamine, when heated under reflux in ethanol, give 2-methylbenzimidazole hydrochloride in high yield (65). o-Toluylenediamine and ethyl -chloroacetoacetate lead to 2,5(or 2,6)-dimethylbenzimidazole (13).…”

Section: N=¿ Ch3mentioning

confidence: 99%

“…When an alcoholic ammonium sulfide solution is used as the reducing agent, yields of "oxbenzimidazoles" as high as [60][61][62][63][64][65][66][67][68][69][70] per cent may be obtained (57,58,548).…”

Section: Lvixmentioning

confidence: 99%