CpCo(CO)2-mediated cyclotrimerisation of bis-alkynes and cyanamides provides multisubstituted 2-aminopyridines, including macrocyclic products, such as 22 (50% yield).

Bleach oxidizes trimethylsilyl cyanide to generate an electrophilic cyanating reagent that readily reacts with an amine nucleophile. This oxidative N-cyanation reaction allows for the preparation of disubstituted cyanamides from amines without using highly toxic cyanogen halides.

N-Alkylnitrilium and N,N-dialkylcyanamidium salts 1 and 2 undergo ene reactions with cyanamides 4 to afford 2-azoniaallene salts 7 and 9 in which the N-alkylnitrilium salts 1 react as the ene, and the cyanamides 4 react as the enophile components. Competing with the ene reaction, N-alkylnitrilium salts 1 undergo [2++2+2] cycloaddition to furnish triazinium salts 8. 2-Azoniaallene salts react wi...

The first one-pot deoxycyanamidation of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more commonly empl...

A fast and convenient synthesis of arylamidines starting from readily available potassium aryltrifluoroborates and cyanamides is reported. The coupling was achieved by Pd(II)-catalysis in a one step 20 min microwave protocol using Pd(O(2)CCF(3)), 6-methyl-2,2'-bipyridyl, TFA, and MeOH, providing the corresponding arylamidines in moderate to excellent yields.

von Braun Cyanogen Bromide Reaction, Solasodine, 13C NMR Solasodine on reaction with BrCN yielded two isomeric cyanamides in a ratio of 3:1, which have been characterised as C-22 configurational isomers, N-cyanosolasodine (22 R, 25 R) I IA and N-cyanosolasodine (22 S, 25 Rj II B on the basis of HI and *3C NMR studies. The same reaction with piperidine, yielded its cyanamide, the 13C NMR of whic...

A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach ex...

The reaction of N-aryl-substituted ketenimines with N,N-disubstituted cyanamides or (MeS)2C=N-CN under high pressure afforded 4-(N,N-disubstituted amino) or 4-(MeS)2C=N-substituted quinazoline derivatives, respectively. These products were formed by [4+2] cycloaddition between the aza-diene moieties of the N-arylsubstituted ketenimines and cyano groups. A 4-(unsubstituted amino)quinazoline deri...