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Three-Component Reaction of Benzothiazole, Acetylenic Esters, Phenoles; Synthesis of Dialkyl 2-benzo[d]thiazol Derivatives Under Grinding

[ Vol. 20 , Issue. 4 ]

Author(s):

Farzaneh Fatemi , Hoorieh Djahaniani and Bita Mohtat   Pages 338 - 345 ( 8 )

Abstract:


Aim and Objective: Due to biological activity of a significant number of compounds containing benzothiazole ring system and in continuation of our interest in developing new environmentally benign methods for the synthesis of heterocyclic compounds by MCRs in this study we performed an efficient three-component from benzothiazole, acetylenic esters and hydroxyl aromatics compounds to synthesize of 2- benzothiazole derivatives in high yield.

Materials and Methods: IR spectra were recorded using an FTIR apparatus. Melting points measured on an Electrothermal 9100 apparatus. Spectra were obtained in solution of CDCl3 using TMS as internal standard. Elemental analyses were carried out using a Heracus CHN–O– Rapid analyzer. A mixture of benzothiazole, dimethyl acetylenedicarboxylate and phenol were placed in a mortar. The mixture was ground with a mortar and pestle at room temperature for 12 min. After completion of the reaction, as indicated by TLC (ethyl acetate: n-hexane, 1: 3), the solvent was distilled off under reduced pressure and the residue was crystallized from diethyl ether.

Results: Treatment of benzothiazole and dialkyl acetylenedicarboxylates in presence of resorcinol and β-naphthol led to products 4 (dialkyl (E)-2-(2-(2-hydroxyphenyl)benzo[d]thiazol-3(2H)-yl-3- methylbut-2-enedioate), while we observed two isomer (Z) and (E) configurations (major and minor) in nearly 70:30 ratio when the reaction was repeated in presence of 8-hydroxy quinolone and DMAD. Also when we examined 2-nitro phenol, 4-nitrophenol, and 4-hydroxy quinoline, only one product 5 was obtained. This indicates that the reaction proceeds efficiently with electron-releasing substituted phenols.

Conclusion: The reaction between benzothiazole and dialkyl acetylenedicarboxylates in the presence of some phenols without electron-withdraw substitution, presents a novel, one-pot, clean, convenient, simple and inexpensive approach into the synthesis of 2-benzothiazole derivatives of potential synthetic and pharmacologically interest. This procedure carries significant advantages because of the minimization of labor, time, and cost.

Keywords:

Three-component reaction, benzothiazole (BZT), 2-benzothiazole derivatives, environmentally benign procedure, solvent-free grinding, biological interesting compounds.

Affiliation:

Department of Chemistry, Karaj Branch, Islamic Azad University, Alborz, Department of Chemistry, East Tehran Branch, Islamic Azad University, PO Box 33955-163, Tehran, Department of Chemistry, Karaj Branch, Islamic Azad University, Alborz



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