4-Functionally Substituted 3-Heterylpyrazoles: XIV. N-Benzyl-N-[3-aryl(heteryl)-4-pyrazolylmethylene]amines and Their Derivatives

Abstract

Reduction with sodium tetrahydridoborate of Schiff bases derived from 3-aryl(heteryl)pyrazole-4-carbaldehydes and benzylamines gave N-benzyl-N-[3-aryl(heteryl)-4-pyrazolylmethylene]amines which were acylated with benzoyl chloride and succinic and maleic anhydrides to obtain the corresponding amides. Treatment of the title compounds with phenyl isothiocyanate afforded substituted thioureas. * For communication XIII, see [1].We previously described [24] a series of new functionalized 3-aryl(heteryl)pyrazole derivatives in which functional substituent is linked to the C 4 atom of the pyrazole ring through a CH 2 or CH unit. The present communication reports on the synthesis and some general transformations of N-benzyl-N-(4-pyrazolyl)methanamines. Except for 3,5-diaminomethyl-1-phenylpyrazole [5], there are no published data on such compounds.

3-[2-Oxo-2H-chromen-3(6)(8)-yl]-1-aryl/heteroaryl-1H-pyrazole-4-carbaldehydes: Synthesis, Reactions and Applications

“…Upon subjection of these hydrazones 2a-x to Vilsmeier-Haack reaction afforded a series of 1-aryl-4-formyl-3-(2-oxo-2H-chromen-3-yl)-1H-pyrazoles (3a-x) (Scheme 1 and Table 1). [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56] Scheme 1 Table 1. The specific reaction conditions for the formation of products 3a-x Also, 3-(2-oxo-2H-chromen-3-yl)-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbaldehydes (5a-n) 41 and 3-(2oxo-2H-chromen-3-yl)-1-(benzothiazol-2-yl)-1H-pyrazole-4-carbaldehydes (8) 57 were synthesized by a sequential Hantzsch thiazole synthesis and Vilsmeier-Haack reaction.…”

Synthesis, antimicrobial, antioxidant, anti-hemolytic and cytotoxic evaluation of new imidazole-based heterocycles

“…The mass spectra were performed using mass Varian MAT CH-5 spectrometer at 70 eV. [22], pyrazolyl aldehydes 13a [23] and 13b [24] were prepared according to the reported procedures.…”

Synthesis and antimicrobial activity of N-benzyl-N-(4-pyrazolylmethyl)-benzenesulfamides

“…The target N-benzyl-N-(4-pyrazoylmethyl)arylsulfamides (IIIa -IIIm) were synthesized by acylating recently reported N-benzyl-N-(4-pyrazolylmethyl) amines Ia -Ig [6] with arylsulfochlorides (IIa, IIb) in the presence of an organic base.…”