Efficient One-Pot Synthesis of Unsymmetrical 2-Thioparabanic Acids from Oxalyl Chloride, Benzoyl Isothiocyanate, and Primary Amines

Abstract

An efficient synthesis of unsymmetrical 2-thioparabanic acids is described via a three-component reaction between benzoyl isothiocyanate and primary amines in the presence of oxalyl chloride.

Synthesis of Pyrroles and Thiazolanes Promoted by N-Methylimidazole in Water

“…29,30 Thus, under similar conditions as for the pyrrole synthesis, we have employed the three-component reaction between alkyl propiolates, primary amines, and isothiocyanates in the presence of a catalytic amount of Nmethylimidazole in water at room temperature to generate thiazolane derivatives 13 31 in good yields (Table 2). 32,33 The structures of compounds 13a-e were apparently from the 1 H NMR, 13 C NMR, and IR spectra which were in agreement with the proposed structures. For example, the 1 H NMR spectrum of 13a displayed two singlets for the NMe protons at δ = 3.24 ppm, the MeO protons appeared as a singlet at δ = 3.75 ppm, and the CH 2 and CH protons appeared as three double doublets at δ = 3.78 ppm, 4.12 ppm, and 4.78 ppm, respectively.…”

ZnO‐NR as the efficient catalyst for the synthesis of new thiazole and cyclopentadienone phosphonate derivatives in water

“…In next step, nucleophilic attack of thiourea 9 to intermediate 8 leads to adduct 10 which undergoes intramolecular cyclization reaction and elimination of phosphate to produce intermediate 12 . Compound 12 by elimination of RCOOH group is produced 13 in water media . Finally compound 5 is generated by oxidation process (Figure ).…”

“…Compound 12 by elimination of RCOOH group is produced 13 in water media. [27] Finally compound 5 is generated by oxidation process ( Figure 4).…”

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

“…Oxalyl chloride also serves as versatile C2 synthon . It has been used as a privileged C(O)CO source in the construction of a wide range of heterocyclic systems with five‐, six‐, seven‐ and eight‐membered rings; for instance, pyrrolediones, isatins, pyrroloisoquinolines, N ‐ω‐chloroalkylisatins, pyrrolopyrazinetriones, imidazolidine‐2,4,5‐trione nucleus, 2‐thioparabanic, furan‐2,3‐diones, thiophene‐2,3‐diones, and oxazolidinedione, as well as oxazolidinetrione . Several reactions have been reported in which oxalyl chloride employed as unexpected and fantastic sources for bond formations, e. g. C−C, OC−CO, C(O)CCl, C(O)C(Cl 2 )O, C(O)CCl 2 , CC(O)Cl, C‐C=O, and C(O)C−O .…”