Synthesis and reactivity of 3-(benzothiazol-2-yl)-3-oxopropanenitrile

Reactivity of 3-(benzothiazol-2-yl)-3-oxopropanenitrile: A facile synthesis of novel polysubstituted thiophenes

“…IR spectra were determined with a Pye Unicam SP 3-300 spectrophotometer (KBr); 1 H NMR spectra were determined with a Varian Gemini NMR spectrometer (200 MHz) with tetramethylsilane (TMS) as internal standard (d in ppm); MS were determined with a Shimadzu GCMS-QP 1000 EX mass spectrometer at 70 eV; Elemental analyses were performed at the Microanalytical Center at Cairo University. 3-(Benzothiazol-2-yl)-3-oxopropanenitrile (1) was prepared according to a published procedure [1]. All compounds gave satisfactory elemental analyses (C, H, N, S, Cl).…”

“…In continuation of our studies on the chemistry of 3-(benzothiazol-2-yl)-3-oxopropanenitrile [1,2,19] and as a part of our program directed toward developing new approaches to a variety of heterocycles incorporating the benzothiazole moiety [1][2][3][4][5] of potential biological activity, we report here the scope and applicability of 3-(benzothiazol-2yl)-3-oxopropanenitrile as a unique precursor for the synthesis of some previously unreported polyfunctionally substituted thiophenes and their fused derivatives in which a benzothiazole ring is incorporated. SCHEME 1 2a-d and elemental sulfur in refluxing dioxane containing a catalytic amount of triethylamine, the thiophene derivatives 3a-c were obtained (Scheme 1).…”

“…Benzothiazole compounds play an important role in modern organic synthesis, not only because they constitute a particularly useful class of heterocyclic compounds [1][2][3][4][5], but also because they are of great biological interest. They have been found to have antiviral [6], antibacterial [7], antimicrobial [8], and fungicidal activities [9].…”

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

“…Similarly to the previous cases, as-triazine ring closure required the presence of nitrile group. There is some controversy in the literature regarding the interpretation of this type of reactions: in some cases the isolation of compounds 84 is reported [49,100,131,145,154,167], while in other cases compounds 85 were isolated [92,108,[168][169][170][171], despite the identical starting materials and reaction conditions.…”

Simple and convenient routes to new polyheterocycles incorporating pyrazole, thiazole, thiophene, and 1,3,4‐thiadiazole moieties

“…Recently, our research program has utilized some reactive-sulfur containing intermediates as versatile building blocks for the synthesis of several thiophene, thiazole, and 1,3,4-thiadiazole derivatives [1][2][3]. In this context, we report herein a convenient route to a variety of polyheterocyclic ring systems incorporating an antipyrin moiety via the reaction of the cyanothioacetanilide derivative 3 with some ␣-halocarbonyl compounds and halohydrazone derivatives.…”