The Uses of Ethyl Cyanobromoacetate in Heterocyclic Synthesis: Novel Synthesis of Thiophene, Pyrazolo[3,4d]thiazole and Thieno[2,3d]pyridazine Derivatives

Abstract

The reaction of active methylene reagents Ia-Ie with phenyl isothiocyanate in basic N,N-dimethylformamide solution followed by cyclization with ethyl cyanobromoacetate II affords the acyclic thioether derivatives IVa-IVe. The use of IVa-IVe in heterocyclic synthesis was described.

Synthesis of Some Novel Thieno[3,2-<i>d</i>]pyrimidines as Potential Cytotoxic Small Molecules against Breast Cancer

“…Compounds 1a, b and 3a are synthesized according to reported methods. 37,47) N-Aryl-2-cyano-3-phenylamino-3-(substituted methylthio)-acrylamides (2a-d) General Procedure: To a cold suspension of finely grinded KOH (1.4 g, 0.025 mol) in DMF (20 mL), N-aryl-2-cyanoacetamides 1a or 1b (0.025 mol) was added and the mixture was stirred at room temperature for 3 h. Phenyl isothiocyanate (3.4 g, 0.025 mol) was added and the mixture was stirred at room temperature for other 3 h. The active methylene chloro derivative (0.025 mol) was then added and the mixture was left on stirring for additional 24 h at room temperature. The mixture was triturated with cold water (ca.…”

Synthesis of Novel Thiophene, Thiazole and Coumarin Derivatives Based on Benzimidazole Nucleus and Their Cytotoxicity and Toxicity Evaluations

“…ration has gained considerable attention in recent years. In view of the above-mentioned facts and in continuation of our interest in the synthesis of heterocycles containing benzimidazole moiety, 25) to identify new candidates that may be value in designing new, potent, selective and less toxic antitumor agents, we report herein the synthesis and anti-tumor evaluation of some novel structure heterocycles incorporating benzo [d] imidazole moiety. For these reasons, we focused our effort in this work through the uses of the 2-(1H-benzo[d]imidazol-2-yl) acetonitrile 1 as the key starting compound.…”