Synthesis and antifungal properties of dithiocarboxylic acid derivatives. II. Novel preparation of 2-alkylamino-1-cyclopentene-1-dithiocarboxylic acids and some of their derivatives

Abstract

2-Methy lamín o-1-cyclopen tene-1-dithiocarboxy lie acid (II) can be obtained in low yield from cyclopentanone with, carbon disulfide and methylamine; no other 2-alkylamino analogs can be synthesized. The amino group of 2-amino-1-cyclopen tene-1-d.ithiocarboxylic acid (I) and that of its methyl ester (VII) can be substituted by the alkylamino group by an amine exchange reaction, yielding the corresponding 2-alkylamino-1-cyclopen tene-1dithiocarboxylic acid (II) or its methyl ester (III-V, VIII-XII), respectively. The structures, including tautomeric forms of the synthesized compounds, were proved by ir and nmr spectroscopy.In previous research it was found that 2-amino-lcyclopentene-l-dithiocarboxylic acid (I) synthesized by Takeshima and coworkers8 exerts a marked antifungal action against various fungi.4 The steric arrangement of the functional groups in this compound permits the formation of six-membered chelates with metals, which fact may be responsible for the biological activity, too. Chelation plays an important role in the

Metal complexes of sulfur–nitrogen chelating agents. V. 2-N-Ethylaminocyclopentene-1-dithiocarboxylic acid complexes of Ni(II), Pd(II), Pt(II), Co(II), Co(III), and Cu(I)

“…between 2-aminocyclopentene-l-dithiocarboxylic acid and These types of ligands are ambidentate in ethylamine adopting the procedure of Bordas et al (8) nature. With ACDA for a large number of with slight modification.…”

Synthesis, physical characterization, antibacterial activity and thermodynamic studies of five coodrdinate cobalt(III) Schiff base complexes

“…The Schiff base ligands, H 2 cd3OMesalMeen, H 2 cd4OMesalMeen, H 2 cd5OMesalMeen, were prepared according to procedures described in the literature [20,[24][25][26]. The complexes shown in Scheme 1 were synthesized as follow: To a refluxing solution of the unsymmetrical ligands (H 2 cd3-, 4-, 5-OMesalMeen) (0.1 mmol) in 10 mL of chloroform/methanol mixture (2:1) under N 2 atmosphere, was added a solution of Co(CH 3 COO) 2 .4H 2 O (1 mmol) in methanol (10 mL) drop wisely.…”

Synthesis, Characterization, Spectral Studies, Antibacterial Evaluation, Thermodynamics and DFT Calculations of Dimethyltin(IV) Dichloride Schiff Base

“…To a solution of half unites ligands methyl-2-{N-(2 × -aminoethane)}-amino-1-cyclopentenedithiocarboxylate (Hcden), 28,29 methyl-2-(1-methyl-2'-aminoethane) amino-1-cyclopentenedithiocarboxylate (HcdMeen) 24,25 and methyl-2-(3-aminopropyl)amino-1-cyclopentenedithiocarboxylate (Hcdpd) 27 (1mmol) in methanol (20 mL) was added, with continuous stirring, diketon's derivatives (1mmol).…”