22706-60-1Relevant academic research and scientific papers
RESEARCH ON 4H-3,1-BENZOXAZINES. 8. SYNTHESIS AND PROPERTIES OF 4H-3,1-BENZOXAZINIUM CHLORIDES
Gromachevskaya, E. V.,Kosulina, T. P.,Kul'nevich, V. G.
, p. 460 - 464 (1993)
A mechanism for the acylation of substituted o-aminophenylcarbinols with carboxylic acid chlorides and the formation of 2-alkyl(aryl, furyl)-4H-3,1-benzoxazinium chlorides is proposed.The nitration and introduction of a sulfur atom into the heterocyclic r
A Novel o-Iminophenyl Anion Route to Heterocycles and Ortho-Substituted Anilines
Katritzky, Alan R.,Zhang, Guifen,Jiang, Jinlong,Steel, Peter J.
, p. 7625 - 7630 (2007/10/03)
Ring opening of lithio derivatives of N-(α-alkoxyalkyl)benzotriazoles 9 and 22 and subsequent extrusion of nitrogen at -78 deg C gave novel o-iminophenyl anions which enable synthetically useful preparations of ortho-substituted anilines (19 and 25) and of benzoheterocycles (14, 20, 21, 24, and 26).
CONVERSIONS OF o-AMINOTRIPHENYLCARBINOL IN THE PRESENCE OF LEWIS ACIDS
Kul'nevich, V. G.,Gromachevskaya, E. V.,Kosulina, T. P.
, p. 776 - 778 (2007/10/02)
9-Phenylacridinium hexahaloantimonates were produced by the action of antimony pentahalides on o-aminotriphenylcarbinol.The presence of halides of carboxylic acids directs the reaction toward the formation of 4,4-diphenyl-1,2-dihydro-4H-3,1-benzoxazinium hexahaloantimonates.
Reactions of 2-Isocyanatobenzoyl Chlorides with Phenylmagnesium Bromide: Synthesis of 2-Phenyl-3,1-benzoxazin-4(H)-ones, N-Benzoyl-2-aminobenzophenones, α-(2-Benzamidoaryl)benzohydrols and 6-Chloro-4,4-diphenyl-3,1-benzoxazin-2(4H)-one
Misra, B. K.,Rao, Y. R.,Mahapatra, S. N.
, p. 908 - 911 (2007/10/02)
In the reaction of 2-isocyanatobenzoyl chloride (Ia) with phenylmagnesium bromide, the isocyanato group is found to be exclusively attacked by the Grignard reagent to give 2-phenyl-3,1-benzoxazin-4(H)-one (IIIa), N-benzoylanthranilic acid (IVa), N-benzoyl-2-aminobenzophenone (Va), and α-(2-benzamidophenyl)benzohydrol (VIa) depending on the mode of addition and the relative amounts of the Grignard reagent.However, in the case of 5-chloro-2-isocyanatobenzoyl chloride (Ib), the chloroformyl group is also found to react simultaneously, although to a smaller extent, to give 6-chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one (VIIb) in addition to 6-chloro-2-phenyl-3,1-benzoxazin-4(H)-one (IIIb), N-benzoyl-2-amino-5-chlorobenzophenone (Vb) and α-(2-benzamido-5-chlorophenyl)benzohydrol (VIb) depending on the reaction conditions.This is presumably due to the decreased reactivity of the isocyanato function due to the chloro group in the para-position.The reaction is believed to proceed through an acyclic intermediate complex which affords IIIa on work-up.PMR data of the compounds have also been discussed.
