ChemInform Abstract: Dimerization of 2‐Arylpropene‐1,1‐dicarbonitriles.

Abstract

The title compounds (I) dimerize in the presence of basic catalysts to form the aminocyclohexadienes (IIa) and (IIb).

Regiochemistry in alkylation, acylation and methoxycarbonylation of alkali salts from 2-substituted alkenylpropanedinitriles

“…The formation of dimer 6 (Scheme 2) is initiated by Michael addition of 4a Ϫ to the neutral carbon acid followed by a multistep ring closure as suggested. 8 Since the spectroscopic parameters of this compound were not completely in line with those reported, a single-crystal X-ray structure analysis was carried out (Fig. 1), showing that their postulated structure was correct.…”

Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

“…This tandem transformation starts with the Knovenagel condensation between the ketone carbonyl of 1 and malononitrile. The resulting product 10 undergoes base-catalyzed dimerization [ 20 , 21 ] to give stabilized carbanion 12 , which is set to add to the adjacent cyano group forming the carbocycle (cf. 13 ).…”

Imidazole‐Mediated Cascade [2 + 2 + 2] Annulation Reactions: A Highly Diastereoselective Synthetic Protocol for the Construction of Multiply Substituted Cyclohexanes

“…However, no reaction occurred upon treatment of 1a with 2f in the presence of imidazole in THF (Scheme ). Moreover, when 2‐(1‐phenylethylidene)malononitrile ( 1j ) was used as the substrate to react with ( E )‐1‐nitrobut‐1‐ene ( 2a ) in the presence of imidazole in THF at room temperature, it was found that the corresponding vinylogous Michael addition product 4 15 and the dimerization product of 1j , which has been identified as compound 5 ,16 were formed in 21 % and 9 % yields, respectively, along with the recovery of the starting materials in 30 % yield, suggesting that the introduction of a substituent in 1 could change the reaction pathway (Scheme ).…”

“…2‐Amino‐6‐methyl‐4,6‐diphenylcyclohexa‐2,4‐diene‐1,1,3‐tricarbonitrile (5): A known compound 16 . 1 H NMR (CDCl 3 , 300 MHz, TMS): δ = 1.91 (s, 3 H, CH 3 ), 5.61 (s, 2 H, NH 2 ), 5.81 (s, 1 H, CH=), 7.40–7.45 (m, 8 H, Ar), 7.61–7.65 (m, 2 H, Ar) ppm.…”