GB1268732A - Process for preparing azoles by ring closure of isocyanates - Google Patents

Process for preparing azoles by ring closure of isocyanates

Info

Publication number
GB1268732A
GB1268732A GB2555270A GB2555270A GB1268732A GB 1268732 A GB1268732 A GB 1268732A GB 2555270 A GB2555270 A GB 2555270A GB 2555270 A GB2555270 A GB 2555270A GB 1268732 A GB1268732 A GB 1268732A
Authority
GB
United Kingdom
Prior art keywords
aryl
alkyl
azoles
temperature
styryl
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
GB2555270A
Inventor
Arthur Gaudens Mohan
Richard Keith Madison
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1268732A publication Critical patent/GB1268732A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Abstract

1,268,732. Preparation of azoles. AMERICAN CYANAMID CO. 27 May, 1970 [30 July, 1969], No. 25552/70. Heading C2C. Compounds of the general formulae wherein X is O, S or -N(R 3 )-: R is alkyl, alkenyl, aralkyl, aryl, styryl, R 1 and R 2 are each H, alkyl, alkoxy, aryl, halo or, when taken together on adjacent C-atoms, -CH=CH-CH=CH-; R 3 is H, alkyl or aryl and Y is alkylene, alkenylene or arylene are prepared by heating a compound where R 4 is alkyl, alkenyl, aralkyl, aryl, styryl or at a temperature of at least 100‹ C. but below the decomposition temperature of the reactant or azole product. The cyclization is preferably effected in the presence of a Lewis acid e.g. iron halide in a solvent such as acetic acid or decalin at a temperature of at least 150‹ C. Amongst the examples o-benzoyloxyphenyl isocyanate is converted to a mixture of 2-phenylbenzoxazole and 3-benzoyl-2-benzoxazolinone, the corresponding benzothiazole derivatives are similarly obtained and 2-phenylbenzimidazole is obtained from o-benzamidophenyl isocyanate.
GB2555270A 1969-07-30 1970-05-27 Process for preparing azoles by ring closure of isocyanates Expired GB1268732A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US84628169A 1969-07-30 1969-07-30

Publications (1)

Publication Number Publication Date
GB1268732A true GB1268732A (en) 1972-03-29

Family

ID=25297433

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2555270A Expired GB1268732A (en) 1969-07-30 1970-05-27 Process for preparing azoles by ring closure of isocyanates

Country Status (6)

Country Link
AU (1) AU1542770A (en)
BE (1) BE754100A (en)
DE (1) DE2037999A1 (en)
FR (1) FR2053292B1 (en)
GB (1) GB1268732A (en)
NL (1) NL7009124A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1584296A (en) * 1976-12-07 1981-02-11 Kanebo Ltd 2-substituted benzimidazole compounds
US4142886A (en) * 1977-06-17 1979-03-06 United States Borax & Chemical Corporation Substituted benzimidazole compounds and use as herbicides
JPS55167282A (en) * 1979-06-12 1980-12-26 Fujisawa Pharmaceut Co Ltd Piperazine derivative or its salt and its preparation
EP0022317B1 (en) * 1979-06-12 1983-09-21 Fujisawa Pharmaceutical Co., Ltd. 2-oxo-benzothiazoline, benzoxazoline or indoline derivatives, their preparation, and pharmaceutical compositions comprising such derivatives
CA1159458A (en) * 1980-03-19 1983-12-27 Hiroshi Ohyama Benzoxazolone derivative, processes for preparation thereof and compositions containing them

Also Published As

Publication number Publication date
AU1542770A (en) 1971-11-25
NL7009124A (en) 1971-02-02
BE754100A (en) 1971-01-29
FR2053292B1 (en) 1973-03-16
DE2037999A1 (en) 1971-02-11
FR2053292A1 (en) 1971-04-16

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