Copper-Catalyzed Reactions of Alkenyl Boronic Esters via Chan-Evans-Lam Coupling/Annulation Cascades: Substrate Selective Synthesis of Dihydroquinazolin-4-ones and Polysubstituted Quinolines was written by Li, Yuge;Cao, Zifeng;Wang, Zhijun;Xu, Liang;Wei, Yu. And the article was included in Organic Letters in 2022.COA of Formula: C7H7FN2O This article mentions the following:
Copper-catalyzed cascade cyclization reactions between alkenyl boronic esters BpinC(R)=CH(R1) [R = H, Me; R1 = Me; RR1 = -(CH2)5-, -(CH2)2O(CH2)2-, -(CH2)2N(C(O)Ot-Bu)(CH2)2-] and N-H-based nucleophiles R2C(O)NHR3 (R2 = 2-amino-5-fluorophenyl, 2-amino-3-bromophenyl, 2-aminophenyl, etc.; R3 = H, Me, Ph, Bn, etc.) have been established, providing new approaches for one-pot assembly of azacycles. Following the Chan-Evans-Lam C-N couplings, the cyclization processes occur via divergent pathways based on the utilized substrates, affording hydroamination product dihydroquinazolin-4-ones I (R4 = H, 6-Me, 8-Br, 7-F, etc.) or aromatization product quinolines II (R5 = Ph, 4-chlorophenyl, Me, etc.; X = H, Cl, Br, F). Via this one-pot C-N coupling/annulation cascade, the target substituted azacycles can be obtained in moderate to good yields in each case. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5COA of Formula: C7H7FN2O).
2-Amino-4-fluorobenzamide (cas: 119023-25-5) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.COA of Formula: C7H7FN2O
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics