169153-14-4

Usage

Uses

Used in Chemical Research and Synthesis:
Methanone, (5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)-, O-methyloxime, (1E)is employed as a key intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical entities.
Used in Pharmaceutical Industry:
Methanone, (5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)-, O-methyloxime, (1E)may have potential applications in the pharmaceutical industry. Its specific properties and reactivity could be harnessed for the development of new drugs and therapeutic agents. Further research and studies are required to explore its potential in this field.
Used in Agrochemical Industry:
Similarly, Methanone, (5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)-, O-methyloxime, (1E)could also find applications in the agrochemical industry. Its unique properties may contribute to the development of novel agrochemicals, such as pesticides, herbicides, or plant growth regulators. Further investigation is needed to determine its suitability and effectiveness in this industry.

Upstream product

• 119-36-8 methyl salicylate 
• 22511-42-8 methyl 2-(2-ethoxy-2-oxoethoxy)benzoate 
• 208711-58-4 benzofuran-3(2H)-one O-methyl oxime 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 93680-80-9 benzofuran-3-yl acetate 
• 635-53-0 (2-carboxyphenoxy)acetic acid 
• 169153-13-3 E-(5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime 
• 200419-35-8 (5,6-dihydro-1,4,2-dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone 
• 593-56-6 N-methoxylamine hydrochloride 
• 200419-33-6 benzofuran-2,3-dione 2-[O-(2-hydroxy-ethyl)-oxime]3-(O-methyl-oxime) 

Downstream Products

• 213265-82-8 (E)-{2-[(6-Chloro-5-fluoro-4-pyrimidinyl)oxy]phenyl}(5,6-dihydro-1,4,2,-dioxazin-3-yl)methanone O-methyloxime 

Relevant academic research and scientific papers

PROCESS FOR PREPARING (E)-(5,6-DIHYDRO-1,4,2-DIOXAZINE-3-YL) (2-HYDROXYPHENYL) METHANONE O-METHYL OXIME

A process for preparing (E)-(5,6-dihydro-l,4,2-dioxazin-3-yl)(2- hydroxyphenyl)methanone O-methyl oxime is described which includes: (i) reacting benzofuran-3(2H)-one O-methyl oxime (1) with at least one nitrite selected from n-butyl nitrite and tert-butyl nitrite, in the presence of a metal alkoxide to form (2Z,32)-2,3-benzofuran-dione O3-methyl dioxime (2) as the predominant isomer; (ii) reacting the (2Z,3Z)-2,3-benzofuran-dione O -methyl dioxime (2) with 2- haloethanol to form (2Z,3Z)-benzofuran-2,3-dione 02-(2-hydroxyethyl) O3 -methyl dioxime (3); and (iii) reacting the (2Z,3Z)-benzofuran-2,3-dione 02-(2-hydroxyethyl) and -methyl dioxime (3) with an acid to form (E)-(5,6-dihydro-l,4,2-dioxazin-3-yl)(2- hydroxyphenyl)methanone (9-methyl oxime (4);

PROCESS FOR PREPARING FLUOXASTROBIN

A process for preparing fluoxastrobin, including: (i) reacting benzofuran-3(2H)-one O-methyl oxime (10) with an alkyl nitrite in the presence of an acid to form (3E)-2,3-benzofuran-dione O3-methyl dioxime (11A) as a predominant isomer; (ii) reacting(3E)-2,3-benzofuran-dione O3-methyl dioxime (11A) with 2-haloethanol to form (3E)-benzofuran-2,3-dione O2-(2-hydroxyethyl) O3-methyl dioxime (12A); and (iii) reacting(3E)-benzofuran-2,3-dione O2-(2-hydroxyethyl) O3-methyl dioxime (12A) with a base to form (E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)methanone O-methyl oxime (13) (iv) reacting a 4,6-di-halo-5-fluoro-pyrimidine (5), wherein X1 is halogen, with (E)-(5,6-dihydro-1,4,2-dioxazin-3-yl)(2-hydroxyphenyl)methanone O-methyl oxime (13), in the presence of a solvent and optionally in the presence of a base, to form an (E)-(2-((6-halo-5-fluoropyrimidin-4-yl)oxy)phenyl)(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyl oxime (14): (v) reacting the (E)-(2-((6-halo-5-fluoropyrimidin-4-yl)oxy)phenyl)(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyl oxime (14) with 2-chlorophenol, in the presence of a solvent and optionally in the presence of a base, to form fluoxastrobin:.

METHOD FOR PRODUCING A DIOXAZINE DERIVATIVE

The invention relates to a novel method for producing 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazines of formula (I), and to a device for carrying out this method.

Process for preparing 3-(1-hydroxphenyl-1-alkoximinomethyl)dioxazines

The present invention relates to a novel process for preparing 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazines which are known as intermediates for preparing compounds having fungicidal properties (WO 95-04728). Furthermore, the invention relates to nove

Intermediates in the preparation of 3-(1-hydroxyphenyl-1-alkoximinomethyl)dioxazines

The single-step preparation of 3-(hydroxyphenyl-1-alkoximinomethyl)dioxazine derivatives of formula (I) from compounds (II), (III) and (V), and the preparation in 2-5 steps from (VII), (VIII), (X), (XI), (XII), (XIV) and (XVI) (via (II), (III) and (V)) are claimed. The preparation of the intermediates is also claimed. The single-step preparations comprise (a) isomerisation of the O-hydroxyethyl-O'-methyl-benzofuran dione dioxime (II) of formula (X'; Q = CZ3Z4CZ1Z2OH; Y = NOA); (b) treatment of the ketone of formula (III) with the alkoxyamine of formula A-O-NH2 (IV) or its acid addition complex, optionally in the presence of a diluent and/or acid acceptor; and (c) by reacting the hydroxylamine of formula (V) with an alkylating agent of formula AX (VI), optionally in the presence of a diluent and/or base. Preparation of (II) comprises (d) reaction of O-hydroxyethylbenzofuran dione monooxime (VII) of formula (X'; Q = CZ3Z4CZ1Z2OH; Y = O) with (IV); (e) reaction of O-alkylbenzofuran dione dioxime (VIII) of formula of formula (X'; Q = H; Y = NOH) with the alcohol of formula Y1CZ3Z4-CZ1Z2-OG (IX); (f) reaction of benzofuran dione mono-oxime (X) of formula (X'; Q = CZ3Z4CZ1Z2OH; Y = NOH) with (VI); or (m) reaction of O-oxyethyl-O'-methyl-benzofurandione dioxime compounds (XIII) of formula (X'; Q = CZ3Z4CZ1Z2OE; Y = NOH) with water or an alcohol, optionally in the presence of acid or base. (VII) is prepared by (g) reaction of (XI) with (IX); or (n) reaction of benzofuran dione mono-oxime (XIV) of formula (X'; Q = CZ3Z4CZ1Z2OE; Y = O). (XIV) is prepared by: (o) reaction of (XI) with ethanol derivatives of formula Y2CZ3Z4CZ1Z2OE (XV), optionally in the presence of an acid acceptor. (VIII) is prepared by: (h) reaction of (XI) with (IV); or (p) reaction of the benzofuran dione dioxime (XII) of formula (X'; Q = H; Y = NOH) with (VI), optionally in the presence of a base. (X) is prepared by: (i) reaction of (VII) with hydroxylamine; or (q) reaction of O-oxyethylbenzofuran dione dioxime (XVI) of formula (X'; Q = CZ3Z4CZ1Z2OE; Y = NOH) with water or an alcohol. (XVI) is prepared by: (r) reaction of (XIV) with hydroxylamine. (XIII) is prepared by: (s) reaction of (XIV) with (IV); (t) reaction of (XVI) with (VI); (u) reaction of (VIII) with (XV). (III) is prepared by: (k) isomerisation of (VII); (V) is prepared by (l) reaction of (III) with hydroxylamine; or (v) reaction of (X). Optionally: reactions are carried out in the presence of diluent, and hydrolyses in base or acid, reaction with alkoxylamine, hydroxylamine or XV) with an acid acceptor; reaction with (IX) or (IX), in base; and isomerisations with acid. A = alkyl; E = acyl or a ketal protection group; R1-R4 = H, halo, CN, nitro, or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl (all optionally substituted by halo); Z1-Z4 = H, alkyl, haloalkyl or hydroxyalkyl; or Z1+Z2, Z1+Z3, Z3+Z4 complete a cycloaliphatic ring; X, Y1, Y2 = halo, alkylsulphonyloxy, alkoxysulphonyloxy or arylsulphonyloxy; G = H; or Y1+G = bond or OCO. (II), (VII), (XIV), (VIII), (X), (XVI), (XIII), (III) and (V) are new.