Abstract
Background: 1,4-Dithiane-2,5-diol (1,4-DTD) is the stable dimer of α-mercapto acetaldehyde. This commercially available ambidentade compound is characterized as having in its chemical structure one group that acts as an electrophile and another that acts as a nucleophile, this permits its use as versatile and efficient synthon in synthetic heterocycle procedures.
Objective: The aim of this review is to present synthetic applications of 1,4-DTD in heterocyclic chemistry and their applicability to the synthesis of bioactive compounds.
Conclusion: Gewald reactions to obtain C-4 and C-5 unsubstituted 2-amino-thiophene derivatives; sulfa- Michael/Henry and sulfa-Michael/aldol sequences to obtain polysubstituted tetrahydrothiophenes, and other heterocyclic reactions that allow synthesizing several functionalized sulfur-containing heterocycles such as thiazolidines, oxathiazinoles and thiazoles are presented and discussed. The use of such heterocyclics in subsequent reactions allows obtaining various bioactive compounds including the antiretroviral lamivudine which is one of the examples presented in this review.
Keywords: 1, 4-dithiane-2, 5-diol, 2-amino-thiophene, Gewald reaction, sulfur heterocycles, sulfanyl carbonyl, tetrahydrothiophene.
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
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