Divergent Approach to Thiazolylidene Derivatives: A Perspective on the Synthesis of a Heterocyclic Skeleton from β-Amidothioamides Reactivity.

Herein we report a domino protocol able to reach regioselectively thiazolylidene systems by combining the reactive peculiarities of both β-amidothioamides (ATAs) and 1,2-diaza-1,3-dienes (DDs). Depending on the reaction conditions and/or the nature of the residue at C4 of the heterodiene system, ATAs can act as hetero-mononucleophiles or hetero-dinucleophiles in the diversified thiazolylidene ring assembly.

[1]  Ming Li,et al.  β-ketothioamides: efficient reagents in the synthesis of heterocycles. , 2015, Organic & biomolecular chemistry.

[2]  Ming Li,et al.  Switching regioselectivity of β-ketothioamides by means of iodine catalysis: synthesis of thiazolylidenes and 1,4-dithiines. , 2014, Chemistry.

[3]  G. Çiftçi,et al.  Synthesis and biological evaluation of thiazoline derivatives as new antimicrobial and anticancer agents. , 2014, European journal of medicinal chemistry.

[4]  A. Srivastava,et al.  DMAP-promoted domino annulation of β-ketothioamides with internal alkynes: a highly regioselective access to functionalized 1,3-thiazolidin-4-ones at room temperature , 2014 .

[5]  R. K. Verma,et al.  DMAP mediated one-pot domino thienannulation: a versatile, regioselective and green mechanochemical route to naphtho[2,3-b]thiophenes , 2013 .

[6]  A. Hassanabadi Synthesis of N-(3-alkyl-4-phenyl-3H-thiazol-2-ylidene)Benzamide Derivatives by Reaction of Phenacyl Bromide and Aroyl Isothiocyanates in the Presence of Primary Amines , 2013 .

[7]  H. Pellissier,et al.  Stereocontrolled domino reactions. , 2013, Chemical reviews.

[8]  G. Giorgi,et al.  Powerful approach to heterocyclic skeletal diversity by sequential three-component reaction of amines, isothiocyanates, and 1,2-diaza-1,3-dienes. , 2012, The Journal of organic chemistry.

[9]  G. Favi,et al.  Direct Access to VariouslySubstituted 2-Imino-4-thiazolines , 2010 .

[10]  G. Favi,et al.  Cultivating the Passion to Build Heterocycles from 1,2‐Diaza‐1,3‐dienes: the Force of Imagination , 2009 .

[11]  Peng-mian Huang,et al.  A Facile and Practical One-PotSynthesis of β-Oxo Thioamides from β-OxoAmides and Isothiocyanates , 2009 .

[12]  G. Giorgi,et al.  Unexpected regioselectivity in the reaction between cycloalkenyl-1-diazenes and thioamides: useful entry to fused cycloalkyl-thiazoline and cycloalkyl-thiazoline–pyrazole systems , 2007 .

[13]  G. Favi,et al.  Efficient synthesis and environmentally friendly reactions of PEG-supported 1,2-diaza-1,3-butadiene. , 2005, Organic letters.

[14]  G. Carvoli,et al.  Facile and High-Yielding Direct Synthesis of 2-Alkyliminothiazolines , 2004 .

[15]  K. Bogdanowicz-Szwed,et al.  Synthesis of Functionalized (2-Thienylcarbonyl)thiazoles and 4-(2-Thienyl)pyridines by Reaction of (2-Thienylcarbonyl)thioacetanilides and their Enamine Derivatives , 2004 .

[16]  A. Fadda,et al.  Utility of isothiocyanates in heterocyclic synthesis , 2002 .

[17]  E. Foresti,et al.  Study of reactions between 1,2-diaza-1,3-butadienes and N,N′-diaryl- or N,N′-dialkylthioureas , 1999 .

[18]  O. Attanasi,et al.  EFFECT OF METAL IONS IN ORGANIC SYNTHESIS; PART XXIII. EASY AND HIGH-YIELD DIRECT SYNTHESIS OF 3-(AMINOCARBONYL)-1-UREIDOPYRROLES BY THE COPPER(II) CHLORIDE-CATALYZED REACTION OF AMINOCARBONYLAZOALKENES WITH 3-OXOALKANAMIDES , 1984 .

[19]  S. Sommer Inverse diels-alder-reaktionen von azo-alkenen mit alkenen☆ , 1977 .