Reactions of isocyanates with 1-cyanothioformanilide

Reactivity of cyanothioformamides and 3‐(4‐bromophenyl)‐5‐imino‐4‐oxazolidinethione toward ortho‐substituted nucleophiles

“…A literature survey reveals that cyanothioformamides, which contain a potentially nucleophilic nitrogen atom ␣ to a cyano function ␣ group, are versatile reagents which have been extensively utilized in heterocyclic synthesis [1][2][3]. The present contribution represents an extension of our recent work [4][5][6][7] on cyanothioformamides 1 and deals with their reactivity toward ortho-substituted anilines to furnish fused heterocycles.…”

Halogenated, alkylated and new types of imidazolidine, pyrrolidine, imidazotriazine and thienoimidazole derivatives with biological and antitumor activities

“…Also, the spectral data are collected in table 5. Cyanothioformanilides (1a-e) were prepared [3,20], 4-iodo-(1f) and 3-isothiocyanato-4-methyl (3) cyanoathioformanilides and 2,4-bis-(cyanothioformamido)toluene (8) were similarly prepared.…”

“…A variety of heterocyclic ring closure reactions of cyanothioformamides [1][2][3] gave rise to imidazole [4], oxazole [5], thiazole [6,7] and other heterocycles [8][9][10][11]. Our interest in the chemistry of cyanothioformamide [12][13][14][15][16] led us to synthesize various types of cyanothioformamides containing aliphatic, aromatic and heterocyclic [17] moieties as well as sulpha derivatives [18].…”

“…Thus, interaction of equimolar amounts of 2,4-bis(isothiocyanato)toluene 2 [27] and potassium cyanide at room temperature [3] furnished a product which its elemental and spectral data were compatible with structure 3 (scheme 1) as 4-methyl-3-isothiocyanatocyanothio-formanilide.…”

A comparative study of the behavior of cyanothioformamide and oxazolidine (thiones or iminothiones) towards some binucleophiles

“…Cyanothioformamides (I) [1,2] have been used widely for syntheses of heterocyclic compounds, such as imidazoles [3], oxazoles [4], and thiazoles [5,6]. Our program on ring-closure reactions [7], activated nitriles [8], and the chemistry of cyanothioformamides [9][10][11][12] led us to react I with chalcones, maleimides, and acetylenedicarboxylic acid to give the corresponding pyrroles [13].…”