Reaction of Dimethylphenacylsulfonium Bromide with N-Nitrosoacetarylamides and Reactions of the Products with Nucleophiles

Abstract

The azo coupling of dimethylphenacylsulfonium bromides (I) with N-nitrosoacetanilides in nonaqueous solvents, and with diazotized aniline in aqueous media gave 2-bromophenylglyoxal 2-arylhydrazones (V) and the tetrazine (VI), respectively. V reacted with nucleophiles displacing the bromide. Treatment of V with bases gave VI via benzoylphenylnitrilimine (X). 1,3-Dipolar cycloadditions of X onto ethyl acrylate and acrylonitrile afforded the expected cycloadducts. The mechanisms of the reactions are outlined.

HETEROAROMATIZATION WITH SULFONAMIDO PHENYL ETHANONE: PART (IV). SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW N-ETHYL-N-METHYLBENZENESULFONAMIDE, 1,3,4-THIADIAZOLE, 1,3,4-THIADIAZINE, 4-OXOTHIAZOLIDINE AND PYRAZOLO[5,1-c][1,2,4]TRIAZINE DERIVATIVES

“…IR spectrum of 11 showed absorption bands at 3169 cm -1 for NH group and 2262 cm -1 for CN group, while 1 H NMR spectrum of 11 showed singlet at δ 2.29 ppm for CH3-C=N, singlet at δ 4.26 ppm for CH2CN and singlet at δ 11.18 ppm for NH group. Interaction of hydrazonecarbodithioate derivative 7 with hydrazonoyl bromides 12a,b [28][29][30] in ethanol containing triethylamine gave the corresponding 1,3,4-thidiazole derivatives 15a,b, respectively. The formation of 15a,b can be rationalized via elimination of methylmercaptan from the corresponding cyclo adduct intermediates 14a,b, which is assumed to be formed from 1,3-dipolar cyclo addition of nitrileimines to the thiocarbonyl double bond.…”

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

“…Elemental analyses were carried out at the Micro analytical Center of Cairo University. 6,7-dimethoxy-3,4-dihydroisoqinoline-1-acetonitrile 1 (Osbond, 1951) and the hydrazonoyl halides 13a (Eweiss & Osman, 1980), 13b (Shawali & Abdelhamid, 1976) and 15 (Shawali et al 1975) were prepared as previously described.…”

Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents

“…All reactions were followed by TLC (silica gel coated aluminum sheets 60 F254, Merck, Merck & Co., Inc., Kenilworth, NJ, USA). Hydrazonoyl halides were prepared as reported in the literature [43][44][45][46]. To a mixture of 1-(1H-indol-3-yl)-3-(p-tolyl)prop-2-en-1-one (3a) (2.61 g, 10 mmol) and thiosemicarbazide (0.92 g, 10 mmol) in EtOH (20 mL), a catalytic amount of triethylamine (1 mL) was added, then heated under reflux for 6 h. The resulting solid was collected, washed with EtOH and recrystallized from acetic acid to give pure 5 as white solid (74% …”