Lewis acid catalyzed reactivity switch: pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes

Abstract

Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes, and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines...

Nickel‐Catalyzed Sequential Dehydrogenation and Cyclization of 2‐Amino(Nitro)‐benzyl Alcohols with Alkyl Alcohols: Synthesis of C‐3‐Substituted Quinolines

“…3 ‐ ( p ‐ tolyl)quinoline ( 3 b ) [18] . Following the general procedure A and E, the title product was obtained as a white solid.…”

“…Yield: 82 %, (35 mg); 1 H NMR (500 MHz, Chloroform-d) δ 8.78 (d, J = 1. 8 [18] Following the general procedure B, the title product was obtained as a colourless liquid. Yield: 71 %, (33 mg); 1 H NMR (500 MHz, Chloroform-d) δ 8.70 (d, J = 1.9 Hz, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.83 (s, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.57 (dd, J = 11.2, 4.1 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H), 2.72 (t, J = 7.7 Hz, 2H), 1.62 (t, J = 7.7 Hz, 2H), 1.33 (dd, J = 15.0, 7.4 Hz, 2H), 0.88 (t, J = 7.4 Hz, 3H).…”

“…; 13 C{1H} NMR (125 MHz, Chloroform-d) δ 150.0, 147.3, 137.9, 133.9, 133.3, 129.4, 129.3, 129.2, 128.2, 128.1, 128.0, 127.5, 127.0. [18] Following the general procedure A and E, the title product was obtained as a white solid. Yield: 76 %, (42 mg); 1 H NMR (500 MHz, Chloroform-d) δ 9.…”

“…Yield: 76 %, (42 mg); 1 H NMR (500 MHz, Chloroform-d) δ 9. 18 (3 c). [18] Following the general procedure A, the title product was obtained as a white solid.…”

Acid-Mediated Cascade Cyclization Pathway to Indeno[2,1-c]chromen-6(7H)-ones

“…For instance, the Lewis/Brønsted acid-mediated cascade or domino organic transformation reaction for synthesizing valuable carbocyclic and heterocyclic organic frameworks from reasonably simple starting materials is a powerful tool in organic chemistry. ,,− In this context, in 2012 and 2013, the Dattatraya group reported the iron­(III) chloride-induced synthesis of indene skeleton-based molecules starting from the o -alkene-tethered cinnamates, and in 2015, the same research group described the synthesis of indanone molecules from ortho -carbonyl-tethered cinnamates via iron­(III) chloride-mediated cyclization. As a continuation, Balamurugan et al in 2021 presented the triflic acid-catalyzed domino cyclization pathway for synthesizing indene derivatives.…”