(Z)-N³-(2-amino-1,2-dicyanovinyl)formamidrazone: a precursor in the synthesis of 1,5-diaminoimidazoles and 6-carbamoyl-1,2-dihydropurines

A New Approach to the Synthesis of N,N‐Dialkyladenine Derivatives

“…The reaction mixture was maintained at r.t. under magnetic stirring until TLC indicated that the starting material was no longer present. The light green solid was filtered, washed with diethyl ether, and identified as the title compound (0.31 g, 2.10 mmol, 68 % 17 mmol) was added to a suspension of 5-amino-4-cyanoformimidoylimidazole [14] (1a; 0.29 g, 2.12 mmol) in acetonitrile (5 mL). The red solution was stirred at r.t., and after 15 min, the solvent was removed in vacuo.…”

“…[14,15,21,24] NMR spectra were recorded with a Varian Unity Plus, including the 1 H-13 C correlation spectra (HMQC and HMBC). IR spectra were recorded with a FT-IR Bomem MB 104 by using nujol mulls and NaCl cells.…”

“…The amino group is incorporated by S N Ar of the halogen atom. [13] In our research group, we have been studying the reactivity of 5-amino-4-cyanoformimidoyl imidazoles 1, which proved to be versatile precursors to 6-substituted purines [14][15][16][17][18][19][20][21][22] and other fused nitrogen heterocycles. [23] The cyanoformimidoyl unit plays a fundamental role in the reactivity of these compounds.…”

Guanidine: studies on the reaction with ethyl N-(2-amino-1,2-dicyanovinyl)formimidate

“…The initial step of the reaction sequence (Scheme 1) is the formation of an amidine 3 from the reaction of imidate 1 and a primary amine 2. Ammonia, 6 alkyl 7 and aryl 8 amines, hydrazines 9 and hydroxylamine ethers 10 have successfully been used in this reaction and the resulting amidine was isolated in two different tautomeric forms (3A and 3B). A combination of different configurations can also be envisaged for the amidine function but this seems to have little influence on the intramolecular cyclization reaction to generate the substituted imidazole 4 or 5 upon addition of base.…”

A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine

“…Cyanoformimdoyl imidazole 4 is considered a straightforward and convenient precursor for fused nitrogen heterocycles [22][23][24][25][26]. The generation of fused imidazoles is initiated at a cyanoformimidoyl unit in the 4-position of the imidazole ring [20].…”