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1,4-Dithiane-2,5-diol: A Versatile Synthon for the Synthesis of Sulfur-containing Heterocycles

[ Vol. 15 , Issue. 8 ]

Author(s):

Isadora Silva Luna, Rayssa Marques Duarte da Cruz, Ryldene Marques Duarte da Cruz, Rodrigo Santos Aquino de Araújo and Francisco Jaime Bezerra Mendonça-Junior*   Pages 1026 - 1042 ( 17 )

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.

Affiliation:

Laboratory of Synthesis and Drug Delivery, Biological Sciences Department, State University of Paraíba, Joao Pessoa, Laboratory of Synthesis and Drug Delivery, Biological Sciences Department, State University of Paraíba, Joao Pessoa, Laboratory of Synthesis and Drug Delivery, Biological Sciences Department, State University of Paraíba, Joao Pessoa, Laboratory of Synthesis and Drug Delivery, Biological Sciences Department, State University of Paraíba, Joao Pessoa, Laboratory of Synthesis and Drug Delivery, Biological Sciences Department, State University of Paraíba, Joao Pessoa

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