Ionic Liquid-Mediated One-Pot 3-Acylimino-3H-1,2-dithiole Synthesis from Thiocarboxylic Acids and Alkynylnitriles via In Situ Generation of Disulfide Intermediates.

A practical and straightforward strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This operationally simple protocol offers an easy and rapid access to a library of dithiol derivatives in moderate to good yields. The mechanistic studies show a benzoyldithio anion addition to alkynylnitriles followed by an annulation reaction through the involvement of a disulfide moiety as the key intermediate.

[1]  O. Rakitin.  Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones , 2021, Molecules.

[2]  F. Glorius,et al.  Bifunctional reagents in organic synthesis , 2021, Nature Reviews Chemistry.

[3]  Wangze Song,et al.  Visible Light-Induced Amide Bond Formation. , 2019, Organic letters.

[4]  A. Goswami,et al.  Syntheses and Applications of 2‐Alkynylnitriles , 2019, Asian Journal of Organic Chemistry.

[5]  Y. Nelyubina,et al.  Synthesis of 6,7-Dihydropyrrolo[2,1-c ][1,3]thiazino[3,2-a ]pyrazine-4(11bH )-(thi)ones from 1,2-Dithiolo-3-(thi)ones , 2019, European Journal of Organic Chemistry.

[6]  Li Tang,et al.  Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis. , 2019, ChemSusChem.

[7]  Yan Du,et al.  Copper-catalyzed direct cyanation of terminal alkynes with benzoyl cyanide , 2018, Tetrahedron Letters.

[8]  Jian Cheng,et al.  Synthesis and biological evaluation of novel hydrogen sulfide releasing nicotinic acid derivatives. , 2016, Bioorganic & medicinal chemistry.

[9]  S. Qiu,et al.  Potassium Thioacids Mediated Selective Amide and Peptide Constructions Enabled by Visible Light Photoredox Catalysis , 2016 .

[10]  Hongxing Jin,et al.  Copper mediated oxidative coupling between terminal alkynes and CuCN , 2015 .

[11]  A. Poso,et al.  Evaluation of the antiviral efficacy of bis[1,2]dithiolo[1,4]thiazines and bis[1,2]dithiolopyrrole derivatives against the nucelocapsid protein of the Feline Immunodeficiency Virus (FIV) as a model for HIV infection. , 2014, Bioorganic & medicinal chemistry letters.

[12]  T. Torroba,et al.  Synthesis of pyrrolidine-fused 1,3-dithiolane oligomers by the cycloaddition of polycyclic dithiolethiones to maleimides and evaluation as mercury(II) indicators. , 2014, The Journal of organic chemistry.

[13]  N. Alkayed,et al.  Differential mechanisms underlying neuroprotection of hydrogen sulfide donors against oxidative stress , 2013, Neurochemistry International.

[14]  Vinod Kumar,et al.  Unique Versatility of Ionic Liquids as Clean Decarboxylation Catalyst Cum Solvent: A Metal‐ and Quinoline‐Free Paradigm towards Synthesis of Indoles, Styrenes, Stilbenes and Arene Derivatives under Microwave Irradiation in Aqueous Conditions , 2008 .

[15]  J. Alemán,et al.  Efficient synthesis of disulfides by air oxidation of thiols under sonication , 2008 .

[16]  Sang -Geon Kim,et al.  Abrogation of Hyperosmotic Impairment of Insulin Signaling by a Novel Class of 1,2-Dithiole-3-thiones through the Inhibition of S6K1 Activation , 2008, Molecular Pharmacology.

[17]  P. Steel,et al.  Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S⋯O interactions , 2007 .

[18]  W. Geiger,et al.  Synthese von 3‐Aminoisothiazolen , 1977 .

[19]  W. Geiger,et al.  Über 3‐Acylimino‐3H‐1.2‐benzodithiole , 1968 .

[20]  H. Behrinǵer,et al.  Über 3‐Aza‐6a‐thia‐thiophthene , 1967 .

[21]  R. Čmelík,et al.  Transformation of 1,2-Dithiole-3-thiones Into 1,6,6aλ4-Trithiapentalenes via Reaction with Bromoethanones , 2006 .

[22]  W. M. Abdou,et al.  An approach to biologically important S‐heterocycles, dithiocarbamyls, and their relevant phosphono derivatives , 2005 .

[23]  J. Marek,et al.  Syntheses and Structure Study on 3,3aλ4,4-Trithia-1-azapentalenes and Their 3-Oxa Analogues , 2003 .