GB1285711A - New benzoxazine derivatives - Google Patents

New benzoxazine derivatives

Info

Publication number
GB1285711A
GB1285711A GB5316868A GB5316868A GB1285711A GB 1285711 A GB1285711 A GB 1285711A GB 5316868 A GB5316868 A GB 5316868A GB 5316868 A GB5316868 A GB 5316868A GB 1285711 A GB1285711 A GB 1285711A
Authority
GB
United Kingdom
Prior art keywords
general formula
hydrogen atom
atom
alkyl
dihydro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5316868A
Inventor
Marcel Pesson
Henri Techer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratoire Roger Bellon SA
Original Assignee
Laboratoire Roger Bellon SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratoire Roger Bellon SA filed Critical Laboratoire Roger Bellon SA
Priority to GB5316868A priority Critical patent/GB1285711A/en
Priority to FR6936403A priority patent/FR2024816B1/fr
Publication of GB1285711A publication Critical patent/GB1285711A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1285711 2 - Carbamoyl - 3 - oxo - 2,3 - dihydro - 1,4 - benzoxazines LABORATOIRE ROGER BELLON 10 Nov 1969 [8 Nov 1968] 53168/68 Heading C2C Novel 2 - carbamoyl - 3 - oxo - 2,3 - dihydro- 1,4-benzoxazines of the general formula wherein R 1 and R 2 are each a hydrogen atom or a C 1-6 alkyl, cycloalkyl or optionally substituted aryl group, or R 1 and R 2 , together with the nitrogen atom to which they are attached form a heterocyclic radical wherein the heterocyclic ring contains 5 or 6 ring members, which ring may include a hetero atom in addition to the nitrogen atom; R 3 is a hydrogen atom or a C 1-6 alkyl or -CH 2 CONR 6 R 7 group, in which R 6 and R 7 are each a hydrogen atom or C 1-6 alkyl group or NR 6 R 7 is a morpholino or piperidino group; and R 4 and R 5 are each a hydrogen or halogen atom or a C 1-6 alkyl or C 1-6 alkoxy group, are prepared (i) when R 3 is a hydrogen atom, by (a) condensing an alkali metal salt of an o-nitrophenol of the general formula wherein M is an alkali metal, with a C 1-6 alkyl halomalonate of the general formula XCH(COOR<SP>11</SP>) 2 , wherein X is a halogen atom and R 2 is a C 1-6 alkyl group, (b) reductively cyclizing the resulting alkyl o-nitrophenoxymalonate of the general formula and (c) reacting the resulting 2-carbalkoxy-3- oxo - 2,3 - dihydro - 1,4 - benzorazine of the general formula with ammonia or an amine of the general formula R 1 R 2 NH; (ii) when R 3 is a hydrogen atom and R 1 and R 2 are not hydrogen atoms, by (a) condensing an alkali metal salt of an o-nitrophenol of the second general formula above with a halomalondiamide of the general formula CXH(CONR 1 R 2 ) 2 , (b) reducing the resulting oitnrophenoxymalondiamide of the general formula and (c) cyclizing the resulting o-aminophenoxymalondiamide of the general formula by heating in an acid medium; (iii) when R 3 is a hydrogen atom and R 1 and R 2 are not hydrogen atoms, by (a) condensing an alkali metal salt of an o-nitrophenol of the second general formula above with a halomalonic ester-amide of the general formula XCH(COOC 2 H 5 ) (CONR 1 R 2 ) and (b) reductively cyclizing the resulting 0-nitrophenoxymalonic ester-amide of the general formula and (iv) when R 3 is other than a hydrogen atom, by reaction of an alkali metal salt of the corresponding 2 - carbamoyl - 3 - oxo - 2,3 - dihydro- 1,4-benzoxazine of the first general formula above wherein R 3 is a hydrogen atom with a compound of the general formula R 3 X, wherein R 3 is other than a hydrogen atom. Bromomalondiamides of the seventh general formula above (X is a bromine atom) are prepared by reaction of a malondiamide of the general formula CH 2 (CONR 1 R 2 ) 2 with bromine in carbon tetrachloride. Bromomalonic esteramides of the tenth general formula above (X is a bromine atom) are prepared analogously. Pharmaceutical compositions having analgesic, anticonvulsant and hypnotic activity comprise, as active ingredient, a 2-carbamoyl-3- oxo-2,3-dihydro- 1 4-benzoxazine of the first general formula above, in association with a pharmaceutical carrier.
GB5316868A 1968-11-08 1968-11-08 New benzoxazine derivatives Expired GB1285711A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5316868A GB1285711A (en) 1968-11-08 1968-11-08 New benzoxazine derivatives
FR6936403A FR2024816B1 (en) 1968-11-08 1969-10-23

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5316868A GB1285711A (en) 1968-11-08 1968-11-08 New benzoxazine derivatives

Publications (1)

Publication Number Publication Date
GB1285711A true GB1285711A (en) 1972-08-16

Family

ID=10466865

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5316868A Expired GB1285711A (en) 1968-11-08 1968-11-08 New benzoxazine derivatives

Country Status (2)

Country Link
FR (1) FR2024816B1 (en)
GB (1) GB1285711A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9101634B2 (en) 2010-05-20 2015-08-11 Shandong University Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2565976B1 (en) * 1984-06-18 1987-05-15 Roussel Uclaf NOVEL 3-OXOBENZOXAZINE DERIVATIVES, SALTS THEREOF, PROCESS FOR THEIR PREPARATION, APPLICATION AS MEDICAMENTS, AND COMPOSITIONS CONTAINING THEM
AU638154B2 (en) * 1990-10-04 1993-06-17 Suntory Limited Benzoxazine derivative and herbicide containing same as an active ingredient

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1173942A (en) * 1967-06-06 1969-12-10 Bellon Labor Sa Roger New 2,3-Dihydro-1,4-Benzoxazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9101634B2 (en) 2010-05-20 2015-08-11 Shandong University Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells

Also Published As

Publication number Publication date
FR2024816B1 (en) 1974-03-22
FR2024816A1 (en) 1970-09-04

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees