New Synthesis of DimethylN-Aroylcarbimidodithioates and 3-Aryl-5-methylthio-1H-1,2,4-triazoles

Hydrogen-bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates

“…O,S-Dialkyl aroylimidothiocarbonates are structural analogues of S,S-dialkyl aroylimidothiocarbonates, which have been widely used as synthetic starting materials (Augustín et al, 1980;Sato et al, 1981;Fukada et al, 1985Fukada et al, , 1986Fukada et al, , 1990Insuasty et al, 2006Insuasty et al, , 2008. We report here the structures of two O-ethyl aroylthiocarbamates, (I) and (II) (Figs.…”

An α‐hydrazinoalkylphosphonate as building block for novel N‐phosphonoalkylheterocycles

“…The preparations of 1,1-dicyano-2-ethoxylethene (6) [5], 1,1-di(benzylthio)-2,2-dicyanoethene (5) [6], and N-dimethylthiomethylene benzoyl amide (4) [7] have been reported before. N-Phosphonoalkylpyrazoles 8 and 9 were synthesized from the cyclization reaction of 3 with 5 and 6 respectively in mild conditions as shown in Scheme 2.…”

Intramolecular Formation of Zwitterionic Intermediates in 1,3-Diaza-Claisen Rearrangements

“…All these combined results suggested that perhaps we needed a different, less reactive, carbon­(IV) source than an isocyanate and a different carbodiimide precursor than a thiourea. Aryl sulfonyl S , S -dimethyl carbodithioimidates seemed ideal reagents for our purposes as they are far less reactive than isothiocyanates and react with amines to give isothioureas that can be readily converted to carbodiimides with thiophilic metals. − Indeed, the amine 15 reacted with carbodithioimidates 19 − 21 to give the corresponding isothioureas 22 – 24 bearing a range of electron withdrawing groups to allow determination of the electron-withdrawing group effect on the rearrangement. , …”

“…8−11 Indeed, the amine 15 reacted with carbodithioimidates 19−21 to give the corresponding isothioureas 22−24 bearing a range of electron withdrawing groups to allow determination of the electron-withdrawing group effect on the rearrangement. 12,13 With the synthesis of the analogues with a three-carbon-tether between aza-norbornene and the isothiourea complete, attention was refocused on completing the synthesis of the two-and fourcarbon-tethered analogues. Reaction of glycine methyl ester hydrochloride with aqueous formaldehyde and cyclopentadiene afforded aza-norbornene 25 in 83% yield through the hetero-Diels−Alder reaction (Figure 4).…”