Abstract
Background: 2-Substituted benzothiazoles are a class of heterocyclic compounds that have a wide range of applications in agriculture, pharmaceutical and chemical industry due to their wide spectrum of biological and biophysical properties. Benzothiazole is usually prepared by the condensation of 2-aminobenzenethiols or 2,2'-disulfanediyldianilines, the cyclization of thioformanilides, or the sulfurization of 2-haloanilides. Furthermore, in the reaction of 2,2'-disulfanediyldianilines with aldehydes to prepare benzothiazole, the S-S bond cleavage is the key to the construction of C-S bond.
Method: 2-Arylbenzothiazoles could be successfully synthesized from the reaction of 2,2'-disulfanediyldianilines with aldehydes by using easily available Na2S·9H2O as a catalyst under microwave irradiation in low power. Results: A novel methodology for preparing 2-arylbenzothiazoles from disulfides and aromatic aldehydes under microwave irradiation in the presence of Na2S has been reported. The reaction mechanism was determined by 1HNMR in detail. It is found for the first time that the S-S bond of the Schiff base could be cleaved by Na2S·9H2O and subsquent could cyclize to form the corresponding 2-arylbenzothiazole. Conclusion: 2-Substituted benzothiazoles were synthesized efficiently via the condensation of 2,2'- disulfanediyldianiline with aromatic aldehydes catalyzed by Na2S·9H2O under microwave irradiation. This methodology provides a green and general synthetic route to prepare benzothiazole with short reaction time, low microwave irradiation power, and high-yield.Keywords: 2-arylbenzothiazole, disulfide cleavage, aldehydes, microwave irradiation, Schiff base.
Graphical Abstract
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
29
3