Cyanoaroylation of Imines Bearing a Thiazole Ring using Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source

Abstract

The efficient and environmentally friendly cyanoaroylation of imines bearing a thiazole ring via a one-pot three-component condensation of N-arylidenethiazol-2-amines, aroyl chlorides and potassium hexacyanoferrate(II) is described. This protocol has the advantages of using an eco-friendly cyanide source, a simple work-up procedure and affords high yields of products.

Eco-Friendly Mono-1,4-Hydrocyanation of Diarenyl Ketones Using Potassium Hexacyanoferrate(II) as a Cyanide Source

“…Recently, K 4 [Fe(CN) 6 ] has been used as a cyanide source for some substitution reactions to synthesise benzonitriles, [11][12][13] aroyl cyanides, 14 benzyl cyanides, 15 and arylsulfonyl cyanides. 16 Our current research focused on the cyanation of unsaturated compounds including C=O, [17][18][19][20] C=N [21][22][23][24][25][26] and/or C=C [27][28][29] by nucleophilic addition reactions using K 4 [Fe(CN) 6 ] as an eco-friendly cyanide source. As an extension of this work, we here report an efficient method for the selective (conjugate) mono-1,4-hydrocyanation of unsaturated compounds bearing one C=O and two C=C bonds, a series of diarenyl ketones, using K 4 [Fe(CN) 6 ] as a selective 1,4-nucleophilic addition reagent and an eco-friendly cyanide source.…”

Conversion of N-Benzyloxycarbonylamino- and N-Tosylamino-Benzyl Phenylsulfones by Green Strecker Reactions to α-Aminobenzyl Nitriles Using Potassium Hexacyanoferrate(II)

“…Recently, K 4 [Fe(CN) 6 ] has been used as a cyanide source for some substitution reactions to synthesise benzonitriles, [11][12][13][14] aroyl cyanides, 15 arylsulfonyl cyanide, 16 benzyl cyanides, 17 and cinnamonitriles. 18 Our research work has focused on the cyanation of unsaturated compounds including C=O, [19][20][21][22] C=N [23][24][25][26] or C=C [27][28] bonds by nucleophilic addition reactions using K 4 [Fe(CN) 6 ] as an eco-friendly cyanide source. Here we report the cyanation of aldimines, generated in situ from N-benzyloxycarbonylamino-and N-tosylamino-benzyl phenylsulfones, to the corresponding N-benzyloxycarbonyl and N-tosyl α-aminobenzyl nitriles by Strecker reactions using potassium hexacyanoferrate(II) as an eco-friendly cyanide source, benzoyl chloride as a promoter, and potassium hydroxide as a base.…”