Synthesis of Bicyclic Thiazolidinethiones and Oxazolidinones by Water‐Mediated Multicomponent Reactions (MCR) and Ring‐Closing Metathesis (RCM)

Abstract

Starting with the development of new multicomponent reactions (MCR) in water, hydroxy thiazolidinethiones and oxazolidinones were prepared efficiently in a one‐pot procedure. The reaction was carried out under mild conditions, consistent with the principles of “green chemistry”. These precursors were converted into different dienes containing terminal C–C double bonds by modifying the hydroxy group in one‐ or two‐step sequences. A final ring‐closing metathesis (RCM) reaction led to various classes of unsaturated bicycles.

A three-component reaction for rapid access to underexplored 1,3-thiazine-2-thiones

“…The stoichiometry of the substrates was chosen as reported recently. 9 As related to our previous studies, H 2 O (in the case of thiazolidinethiones) and MeOH (in the case of 2,2dialkyl-and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines) are the solvents of choice. Thus, we tested H 2 O as well as MeOH in combination with different bases-i.e.…”

“…Combining our previous published concept of synthesis of 2,2dialkyl-and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines 3 and thiazolidinethiones 9 the targeted 3,4-dihydro-2H-1,3-thiazine-2-thiones should be obtained in a MCR using β-chlorovinyl aldehydes, primary amines and carbon disulfide. The β-chlorovinyl aldehydes are received by the conversion of α-methylene ketones with DMF and POCl 3 .…”

“…4). 9 The RCMs were performed in toluene using 5 mol% of Ru catalyst A to generate the six-and seven-membered annulated bicycles 6 in yields up to 83% (Scheme 2, products 6a-f ).…”

Novel semicarbazone-based α-amidoalkylating reagents: general synthesis and reactions with <em>H</em>-, <em>O</em>-, <em>S</em>-, <em>N</em>-, and <em>P</em>-nucleophiles

“…Commonly, electrophilic amidoalkylating reagents are based on carboxamides and carbamates [1][2][3]. Their preparation from other amides, e.g., ureas [24][25][26][27], thioureas [28][29][30], guanidines [31][32][33], thio-and dithiocarbamates [34][35][36], amides of various oxoacids of sulfur [37,38] and phosphorus [39,40] has been much less studied. To the best of our knowledge, there are no reports on preparation and application of semicarbazide-based amidoalkylating reagents.…”

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

“…15 General methods for the synthesis of these compounds include the reaction of carbon disulfide with 1,2-amino alcohols, 16 1,2-amino thiols, 17 and aziridines. 18 Recently, the multicomponent reactions of amines and carbon disulfide with biselectrophiles such as arylpropiolates, 19 dialkyl acetylenedicarboxylates, 20 fumaryl chloride, 21 α-chloro-β,γalkenoate esters, 10a α-halo carbonyls 22 and Morita-Baylis-Hillman allylic substrates 23 have proved as efficient strategies for the construction of these heterocycles. Other methods include reactions of propargylic amines with carbon disulfide, 11a iodocyclization of allyl dithiocarbamates with iodine, 24 and reaction of dithiocarbamic acids with nitroepoxides (Scheme1).…”