Facile and mild deprotection of semicarbazones under solvent-free conditions with N,N,N',N'-tetrabromo-benzene-1,3-disulfonylamide

Abstract

[TBBDA] was reacted with semicarbazones and converts them to their corresponding carbonyl compounds in excellent yields under solvent-free conditions.

A New and Facile Protocol for the Synthesis of Dithiocarbamate-linked 3,4-Dihydro-2H-pyran Using N-Halo Catalysts Under Mild Conditions Reaction

“…In a continuation of our interest in the application of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide (TBBDA) and poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) (PBBS), 22 (Scheme 1), in organic synthesis, [23][24][25][26][27][28][29][30][31][32][33][34][35] we wish to report here a facile and improved protocol for preparation of dithiocarbamate derivatives, from amines, carbon disulfide (CS 2 ) and 3,4-dihydro-2H-pyran in the presence of TBBDA and PBBS as catalysts in EtOH/H 2 O at ambient conditions (Scheme 1).…”

Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide

“…Since TBBDA contains bromine atoms which are bonded to nitrogen atoms, it is possible that this catalyst releases Br + in situ, which can act as an electrophilic species [21][22][23][24][25][26]. Therefore, the following mechanism can be suggested for the synthesis of amidoalkyl naphthols (Scheme 2) [16][17][18][19].…”

“…In continuation of our interest in the application of N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] [21] (Fig. 1) in organic synthesis [22][23][24][25][26] we report here a convenient method of a one-pot synthesis of 1-amidoalkyl-2-naphthol derivatives from various aromatic aldehydes, β-naphthol, and urea, carried out with high yields in the presence of TBBDA, at room temperature, and under solvent-free conditions (Scheme 1). This reaction is simple, green, and requires no toxic organic solvents.…”

Regeneration of Carbonyl Compounds by Deoximation of Piperidine-4-one Oximes with Quinolinium Flurochromate in Presence of Montmorillonite K10 Clay

“…The solvent free deoximation of protected carbonyl compounds by ammonium persulphate on silica [7] and regeneration of carbonyl compounds from aromatic semicarbazones by ammonium persulphate impregnated on montmorillonite K 10 clay in microwave or ultra sound irradiation [8] was also reported. Poly[N-bromobenzene-1,3-disulphonamide] [9] is used for the conversion of oximes and semicarbazones in solid state to their corresponding carbonyl compounds [10,11].…”