An efficient synthesis of 2H-1,4-benzoxazin-3(4H)-ones via Smiles rearrangement

Abstract

A novel and effective synthesis of substituted 1,4-benzoxazinones via Smiles rearrangement is described. Treatment of N-substituted 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in refluxing DMF afforded the corresponding substituted 1,4-benzoxazinones in excellent yield.

Synthesis, Antimicrobial, Antioxidant and Docking Study of Novel 2H-1,4-Benzoxazin-3(4H)-One Derivatives

“…This compound was prepared according to the procedure described in reference [8]. A mixture of o-amino phenol (2.18 g,0.02 mol) and anhydrous K 2 CO 3 (0.4g,0.003 mol ) in dry acetone (25ml), chloroacetyl chloride (2.26ml,0.02 mol) was added drop-wise at (0-5 °C).…”

“…Brown powder ; yield 65%, m.p. 155-157 °C, IR (ν/cm - [1,4] oxazin-4-yl)acetamide (8) [1,4]oxazine-4yl) acetamide (9) This compound was prepared according to the procedure described in reference [13]. A mixture of compound 6 (0.001 mol) and Phthalic anhydride (0.001 mol) in dry benzene (20ml).…”

Copper-catalysed cross-coupling affected by the Smiles rearrangement: a new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

“…The Smiles Rearrangement (SR) has been used in the synthesis of different benzoxazinones. [20][21][22][23] To the best of our knowledge there have been no reports of this rearrangement in the synthesis of benzoxazines. In spite of the wealth of literature pertaining to SR, there is still a gap in the literature with regard to studies on the conformational effect on the copper catalysed ring closure via SR.…”