K₂CO₃‐Promoted Ring‐Opening/Cyclization Reactions of Multi‐substituted Donor‐Acceptor Cyclopropanes with Thiourea: Access to 2‐Amino‐4,6‐diarylnicotinonitrile Derivatives

Abstract

The ring-opening/cyclization reactions of substituted 2-acyl-3arylcyclopropane-1,1-dicarbonitriles with thiourea promoted by K 2 CO 3 were investigated successfully. Using the reaction, the desired 2-amino-4,6-diarylnicotinonitrile derivatives were obtained in good to excellent yields. This work provides a new strategy for the synthesis of 2-amino-4,6-diarylnicotinonitrile derivatives.

Stereoselective Synthesis and Application of Gibberellic Acid-Derived Aminodiols

“…Likewise amines, the oxirane ring could only be opened in the presence of K 2 CO 3 owing to the lower reactivity of N -containing heterocycles. A possible reaction pathway through K 2 CO 3 -promoted azole nucleophilicity and subsequent nucleophilic addition to epoxide 3 afforded derivatives 26 – 30 [ 42 ]. The reactions were completely clean, furnishing azole-based aminodiol adducts with moderate to satisfactory yields (45–75%) ( Scheme 4 , Table 2 ).…”

Novel (+)-Neoisopulegol-Based O-Benzyl Derivatives as Antimicrobial Agents

“…Fortunately, it was achieved by reacting 4a with azoles promoted by K 2 CO 3 [ 81 ]. A possible reaction pathway through potassium carbonate-mediated ring-opening reaction of epoxide 4a and subsequent nucleophilic addition afforded O -benzyl derivatives 7a – 8a [ 82 ] . Debenzylation of 5a by hydrogenolysis over Pd/C in MeOH resulted in primary aminodiol 9a in excellent yield.…”

Stereoselective Synthesis of 4,5‐Dihydroisoxazole Derivatives from 1,1‐Dicyanocyclopropanes and Hydroxylamine Hydrochloride

“…Thin layer chromatography (TLC) was used to monitor all reactions. These reported methods were used for the preparation of substituted cyclopropane‐1,1‐dicarbonitriles 7a – 7e , [97–112] other reagents and solvents were purchased from commercial suppliers and purified by standard techniques.…”

“…to construct various carbo‐ and heterocyclic compounds, containing many natural compounds and their analogs. As easily available multifunctional D‐A cyclopropanes, 2‐acyl‐3‐aryl‐cyclo‐propane‐1,1‐dicarbonitriles and 2‐acyl‐3‐aryl‐1‐cyanocyclopropane‐1‐carboxylates [84–96] have attracted wide attention in the classical heterocycle syntheses [97–112] . Considering the driving forces for the development of these new routes, and in continuation of using multifunctional D‐A cyclopropanes in the synthesis of diverse and complex compounds, we envisioned an approach to access functionalized isoxazoline derivatives through a cyclization reaction of substituted 1,1‐dicyanocyclopropane derivatives and hydroxylamine hydrochloride.…”