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1. (WO1998051666) PROCESS FOR THE PREPARATION OF AN OXIRANE, AZIRIDINE OR CYCLOPROPANE
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/051666 International Application No.: PCT/GB1998/001289
Publication Date: 19.11.1998 International Filing Date: 01.05.1998
Chapter 2 Demand Filed: 20.11.1998
IPC:
C07D 203/02 (2006.01) ,C07D 301/02 (2006.01) ,C07D 303/04 (2006.01) ,C07D 303/08 (2006.01) ,C07D 303/22 (2006.01) ,C07D 303/46 (2006.01) ,C07D 327/06 (2006.01) ,C07D 333/54 (2006.01) ,C07D 333/78 (2006.01) ,C07D 405/04 (2006.01) ,C07D 495/08 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
203
Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
02
Preparation by ring-closure
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
301
Preparation of oxiranes
02
Synthesis of the oxirane ring
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
303
Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02
Compounds containing oxirane rings
04
containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
303
Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02
Compounds containing oxirane rings
08
with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
303
Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02
Compounds containing oxirane rings
12
with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
18
by etherified hydroxyl radicals
20
Ethers with hydroxy compounds containing no oxirane rings
22
with monohydroxy compounds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
303
Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02
Compounds containing oxirane rings
38
with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
46
by amide or nitrile radicals
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
327
Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
02
one oxygen atom and one sulfur atom
06
Six-membered rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50
condensed with carbocyclic rings or ring systems
52
Benzo [b] thiophenes; Hydrogenated benzo [b] thiophenes
54
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
50
condensed with carbocyclic rings or ring systems
78
condensed with rings other than six-membered or with ring systems containing such rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
405
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
02
containing two hetero rings
04
directly linked by a ring-member-to-ring- member bond
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
495
Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
02
in which the condensed system contains two hetero rings
08
Bridged systems
Applicants:
AVECIA LIMITED [GB/GB]; Hexagon House Blackley Manchester M9 8ZS, GB (AllExceptUS)
UNIVERSITY OF SHEFFIELD [GB/GB]; Firth Court Western Bank Sheffield S10 2TN, GB (AllExceptUS)
STUDLEY, John, Richard [GB/GB]; GB (UsOnly)
AGGARWAL, Varinder, Kumar [GB/GB]; GB (UsOnly)
Inventors:
STUDLEY, John, Richard; GB
AGGARWAL, Varinder, Kumar; GB
Agent:
REVELL, Christopher; Avecia Limited Intellectual Property Group Hexagon House, P.O. Box 42 Blackley Manchester M9 8ZS , GB
Priority Data:
9709528.509.05.1997GB
Title (EN) PROCESS FOR THE PREPARATION OF AN OXIRANE, AZIRIDINE OR CYCLOPROPANE
(FR) PROCEDE PERMETTANT DE PREPARER DE L'OXIRANE, DE L'AZIRIDINE ET DU CYCLOPROPANE
Abstract:
(EN) A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein X is oxygen, NR4 or CHR5; R1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R2 is hydrogen, alkyl, aryl, heteroaromatic, CO2R8, CHR14NHR13, heterocyclic or cycloalkyl; or R1 and R2 join together to form a cycloalkyl ring; R3 and R10 are, independently, hydrogen, alkyl, aryl, heteroaromatic, CO2R8, R83Sn, CONR8R9, trialkylsilyl or triarylsilyl; R4 is an electron withdrawing group; R5 is alkyl, cycloalkyl, aryl, heteroaromatic, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 or CN; R8 and R9 are independently alkyl or aryl; and R13 and R14 are independently hydrogen, alkyl or aryl is provided. The process comprises degrading a compound of the formula (II), (IIa), (IIb) or (IIc), wherein R3 and R10 are as defined above; Y is a cation; depending on the nature of Y, r is 1 or 2; and L is a suitable leaving group, to form a diazo compound. The diazo compound is reacted with a suitable transition metal catalyst, and the product thereof reacted with a sulphide of the formula SR6R7, wherein R6 and R7 are independently alkyl, aryl or heteroaromatic, or R6 and R7 join together to form an optionally substituted ring which optionally includes an additional heteroatom. This product is then reacted with an aldehyde, ketone, imine or alkene.
(FR) L'invention concerne un procédé permettant de préparer de l'oxirane, de l'aziridine et du cyclopropane, de formule (I), dans laquelle X est oxygène, NR4 ou CHR5; R1 est hydrogène, alkyle, aryle, ou un noyau hétéroaromatique, hétérocyclique ou cycloalkyle; R2 est hydrogène, alkyle, aryle, un noyau hétéroaromatique, CO2R8, CHR14NHR13, un noyau hétérocyclique ou cycloalkyle; ou bien R1 et R2 forment ensemble un noyau cycloalkyle; R3 et R10 sont indépendamment hydrogène, alkyle, aryle, un noyau hétéroaromatique, CO2R8, R83Sn, CONR8R9, trialkylsilyle ou triarylsilyle; R4 est un groupe accepteur d'électrons; R5 est alkyle, cycloalkyle, aryle, un noyau hétéroaromatique, SO2R8, SO3R8, COR8, CO2R8, CONR8R9, PO(R8)2, PO(OR8)2 ou CN; R8 et R9 sont indépendamment alkyle ou aryle; et R13 et R14 sont indépendamment hydrogène, alkyle ou aryle. Le procédé comprend la dégradation d'un composé de formule (II), (IIa), (IIb) ou (IIc), dans laquelle R3 et R10 sont tels que définis ci-dessus; Y est un cation; suivant la nature de Y, r est 1 ou 2; et L est un groupe nucléofuge convenable; pour former un composé diazoïque. On fait réagir ce dernier avec un catalyseur approprié, contenant un métal de transition, puis on fait réagir le produit obtenu avec un sulfure de la formule SR6R7, dans laquelle R6 et R7 sont indépendamment alkyle, aryle ou un groupe hétéroaromatique, ou bien R6 et R7 forment ensemble un noyau éventuellement substitué renfermant éventuellement un hétéroatome supplémentaire. On fait ensuite réagir ce produit avec un aldéhyde, une cétone, une imine ou un alcène.
Designated States: AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, FI, GB, GE, GH, GM, GW, HU, ID, IL, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, US, UZ, VN, YU, ZW
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, SD, SZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
KR1020010012357EP0983236US6559323JP2001527556 CA2289755DE000069818039
PT983236AU1998072251