Synthesis of 4H‐3,1‐Benzoxazines, Quinazolin‐2‐ones, and Quinoline‐4‐ones by Palladium‐Catalyzed Oxidative Carbonylation of 2‐Ethynylaniline Derivatives.

Abstract

Ring closure reactionsRing closure reactions O 0130 Synthesis of 4H-3,1-Benzoxazines, Quinazolin-2-ones, and Quinoline-4-ones by Palladium-Catalyzed Oxidative Carbonylation of 2-Ethynylaniline Derivatives. -(COSTA*, M.; DELLA CA, N.; GABRIELE, B.; MASSERA, C.; SALERNO, G.; SOLIANI, M.; J.

(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine

“…Compound 1 was prepared according to procedures reported in the literature [14]. Other chemicals were obtained from commercial sources and were used without further purification.…”

“…Over the years, we have successfully applied this effective methodology to access carbonylated compounds in a one-pot fashion [6][7][8][9][10][11][12][13]. In particular, some years ago, we reported a facile and efficient route for the synthesis of new functionalized benzo [d] [1,3]oxazines by in situ deprotection of 2-(trimethylsilanyl)ethynylaniline derivatives followed by palladium-catalyzed cyclization-alkoxycarbonylation [14]. The benzo[d] [1,3]oxazine scaffold is found in many biologically active molecules, including anti-tumor, anti-inflammatory, anti-convulsant, and anti-fungal agents [15][16][17][18][19].…”