Title (en) METHOD OF PREPARATION OF DELTA2 N-HETEROCYCLES. Title (de) VERFAHREN ZUR HERSTELLUNG VON DELTA2 N-HETEROCYCLEN. Title (fr) PROCEDE DE PREPARATION DE N-HETEROCYCLES-DELTA2. Publication EP 0078804 A1 19830518 (DE) Application EP 82900092 A 19811214 Priority DE 3047759 A 19801215 Abstract (en) [origin: DE3047759A1] Method of preparation of //c<s2>s N-heterocycles having the general formula I (FORMULA) wherein v is an integer from 1 to 4, R<u1>u represents (if v = 1) hydrogen, one of the following residues: alkyl with 1 to 19 carbon atoms, aralkyl with 7 to 10 carbon atoms or cycloalkyl with 5 to 7 carbon atoms, these residues being optionally substituted by hydroxy, amino, nitro, fluorine, chlorine, bromine, C<u1>u-C<u4>u alkoxycarbonyl, di-C<u1>u-C<u4>u alkylaminocarbonyl, C<u1>u-C<u4>u alkylaminocarbonyl, tri-C<u1>u-C<u4>u alkylsilyloxy, tetrahydropyranyloxy or benzyloxy; or one of the oxo-alkyl with 1 to 6 carbon atoms, aryl residues or an heterocycle having 5 to 6 links with 1 to 3 nitrogen, oxygen or sulphur atoms as heteroatoms; R<u1>u represents (if v = 2) an arylene residue, an alkylene - (CH<u2>u)-<um>u residue, wherein m is 1 to 6, and which may be substituted by hydroxy, oxo, amino, nitro, fluorine, chlorine, bromine, tri-C<u1>u-C<u4>u alkylsilyloxy, or benzyloxy; or the -CH = CH- residue; R represents (if v = 3 or 4) a benzene residue with 3 to 4 free valences or an alkylene - (CH)- residue with 3 to 4 free valences, which may optionally be substituted by hydroxy, oxo, amino, nitro, fluorine, chlorine, bromine, tri-C<u1>u -C<u4>u alkylsilyloxy, tetrahydropyranyloxy, or benzyloxy; D represents an imino residue or a direct link; Y represents an oxygen or sulphur atom, or an imino residue or N-(C<u1>u-C<u4>u alkyl)imino; Z represent the (CR<u6>uR<u7>u)<un>u residue wherein n may be 0 to 3; R represents a hydrogen atom, an alkyl residue with 1 to 6 carbon atoms, optionally substituted by hydroxy or amino; or a C<u1>u-C<u4>u alkoxycarbonyl, cyano or di-C<u1>u-C<u4>u alkylaminocarbonyl residue, R<u3>u, R<u4>u, R<u5>u, R<u6>u, R<u7>u each represent a hydrogen atom, an alkyl residue with 1 to 6 carbon atoms, optionally substituted by hydroxy or amino; or an aryl residue; R<u3>u and R<u4>u represent together a trimethylene, tetramethylene or 1, 3-butadienylene residue, to the extent that R and R represent together a direct link; this method utilizing as starting compounds those having the general formula (FORMULA) wherein R<u1>u, D and v have the above-mentioned meanings, and X represent an oxygen or sulphur atom or the residue (FORMULA) R<u8>u represents hydroxy, a C -C alkoxy residue, a C<u1>u-C<u6>u alkylthio residue, an aryloxy or arylthio residue, an aralkyloxy or aralkylthio residue with 7 to 10 carbon atoms, a C<u1>u-C<u4>u trialkylsilyloxy or C<u1>u-C<u4>u trialkylaralkylsilythio residue; this method utilizing as starting compounds also the amines of general formula (FORMULA) wherein R<u2>u R, R<u4>u, R<u5>u, Y and Z have the above-mentioned meanings; that method is characterized by the fact that the reaction is carried out by means of organic phosphines or of phosphonium salts and perhalogenated hydrocarbons or ketones respectively with azodicarboxylic acid diesters in the presence of tertiary amines. Abstract (fr) Procede de preparation de N-heterocycles-(Alpha)2 de formule generale I, (FORMULE) dans laquelle v signifie un nombre de 1 a 4, R1 signifie (si v = 1) l'hydrogene, l'un des restes suivants: alkyle avec 1 a 19 atomes de C, aralkyle avec 7 a 10 atomes de C ou cyclo-alkyle avec 5 a 7 atomes de C; ces restes etant eventuellement substitues par un hydroxy, amino, nitro, fluor, chlore, brome, C1-C4-alkoxycarbonyle, di-C1-C4alkylaminocarbonyle, C1-C4-alkylaminocarbonyle, tri-C1-C4-alkylsilyloxy-, tetrahydropyranyloxy ou benzoyloxy; ou l'un des restes oxo-alkyle avec 1 a 6 atomes de C, aryle ou un heterocycle a 5 ou 6 chainons avec 1 a 3 atomes N, O ou S en tant qu'heteroatomes; R1 signifie (si v = 2) un reste arylene, un reste alkylene-(CH2)-m, dans lequel m signifie 1 a 6, et qui peut etre substitue par un hydroxy, oxo, amino, nitro, fluor, chlore, brome, triC1-C4-alkylsilyloxy, ou benzoyloxy; ou le reste -CH = CH-; R1 signifie (si v = 3 ou 4) un reste benzene a 3 ou 4 valences libres ou un reste alkylene(CH2)-m a 3 ou 4 valences libres, dans lequel m est 1 a 6 et qui peut etre eventuellement substitue par un hydroxy, oxo, amino, nitro, fluor, chlore, brome, tri-C1-C4-alkylsilyloxy, tetrahydropyranyloxy, ou benzoyloxy; D signifie un reste imino ou une liaison directe; Y signifie un atome d'oxygene, de soufre ou un reste imino ou N-(C1-C4-alkyle)-imino; Z signifie le reste (CR6R7)n, ou n peut etre 0 a 3; R2 signifie un atome d'hydrogene, un reste alkyle avec 1 a 6 atomes de C, eventuellement substitue par un hydroxy ou amino; ou un reste C1-C4-alkoxycarbonyle, cyano ou di-C1-C4alkylaminocarbonyle; R3, R4, R5, R6, R7 signifient chacun un atome d'hydrogene, un reste alkyle avec 1 a 6 atomes de C, eventuellement substitue par un hydroxy ou amino; ou un reste aryle; R3 et R4 en commun un reste trimethylene, tetramethylene ou 1,3-butadienylene, ceci pour autant que R2 et R5 representent en commun une liaison directe; ce procede utilisant comme compose de depart ceux de la formule generale II (FORMULE) dans laquelle R1, Inventor VORBRUEGGEN HELMUT (DE) Applicant SCHERING AG (DE) IPC 1-7 (main, further and additional classification) C07D 263/12; C07D 233/06; C07D 263/14; C07D 263/16; C07D 263/28; C07D 263/56; C07D 265/08; C07D 267/06; C07D 277/10; C07D 277/18; C07D 413/04 IPC 8 full level (invention and additional information) C07D 233/06 (2006.01); C07D 239/06 (2006.01); C07D 263/00 (2006.01); C07D 263/12 (2006.01); C07D 263/14 (2006.01); C07D 263/16 (2006.01); C07D 263/28 (2006.01); C07D 263/56 (2006.01); C07D 265/00 (2006.01); C07D 265/08 (2006.01); C07D 267/00 (2006.01); C07D 267/06 (2006.01); C07D 277/10 (2006.01); C07D 277/18 (2006.01); C07D 413/00 (2006.01) CPC (invention and additional information) C07D 239/06 (2013.01); C07D 233/06 (2013.01); C07D 263/12 (2013.01); C07D 263/14 (2013.01); C07D 263/16 (2013.01); C07D 263/28 (2013.01); C07D 263/56 (2013.01); C07D 265/08 (2013.01); C07D 267/06 (2013.01); C07D 277/10 (2013.01); C07D 277/18 (2013.01) Citation (search report) See references of WO 8202046A1 Designated contracting state (EPC) AT BE CH DE FR GB LI LU NL SE EPO simple patent family WO 8202046 A1 19820624; DE 3047759 A1 19820715; EP 0078804 A1 19830518; JP S57501962 A 19821104 INPADOC legal status 2007-08-08 [RIN1] INVENTOR (CORRECTION) - Inventor name : VORBRUEGGEN, HELMUT 1983-10-12 [18D] DEEMED TO BE WITHDRAWN - Effective date : 19830707 1983-05-18 [AK] DESIGNATED CONTRACTING STATES: - Designated State(s) : AT BE CH DE FR GB LI LU NL SE