REARRANGEMENT REACTIONS .3. SYNTHESES AND DIELS-ALDER REACTIONS OF 2-ALKYLAZO-SUBSTITUTED 1,3-BUTADIENES

被引:27
作者
BANERT, K
HAGEDORN, M
机构
[1] Fachbereich 8 der Universität, Organische Chemie II, W-5900 Siegen
关键词
D O I
10.1016/S0040-4039(00)60179-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Alkyl-1-(2,3-butadienyl)hydrazines 1b,d-g can be oxidized under mild conditions to yield 1-alkyl-2-(1-methylen-2-propenyl)diazenes 3. These E-configurated azo compounds are precursors for rapid inter- and intramolecular [4 + 2] cycloadditions to give the heterocyclic products 4 and 6-10.
引用
收藏
页码:7331 / 7334
页数:4
相关论文
共 16 条
[1]   SYNTHESIS OF NEW 1-ALKOXYCARBONYLAMINO-3-SULFONYLPYRROLES BY REACTION OF (ALKOXYCARBONYLAZO)ALKENES WITH BETA-KETO SULFONES [J].
ATTANASI, O ;
FILIPPONE, P ;
MEI, A ;
SANTEUSANIO, S ;
SERRAZANETTI, F .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (10) :3332-3334
[2]   EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .31. SYNTHESIS OF NEW 3-CARBONYL-1-HETEROCYCLAMINOPYRROLES AND "3-CARBOXY-1-HETEROCYCLAMINOPYRROLES BY COPPER(II) CHLORIDE-CATALYZED REACTION OF HETEROCYCLIC AZOALKENES [J].
ATTANASI, O ;
FILIPPONE, P ;
MEI, A ;
SERRAZANETTI, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (01) :25-28
[3]  
Attanasi O. A., 1986, ORG PREP PROCED INT, V18, P299
[4]   CONJUGATED AZOALKENES .8. REACTION OF SOME CONJUGATED AZOALKENES WITH ACTIVATED NITRILES - SYNTHESIS OF NEW PYRROLO[2,3-B]PYRROLES AND 1,2-DIAMINOPYRROLES - X-RAY MOLECULAR-STRUCTURE OF DIETHYL 6-AMINO-1,6-BIS-(TERT-BUTOXYCARBONYLAMINO)-3A-CYANO-2,5-DIMETHYL-1,3A,6,6A-TETRAHYDROPYRROLO-[2,3-B]PYRROLE-3,4-DICARBOXYLATE [J].
ATTANASI, OA ;
SANTEUSANIO, S ;
SERRAZANETTI, F ;
FORESTI, E ;
MCKILLOP, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1669-1675
[5]   CONJUGATED AZOALKENES .5. FACILE SYNTHESIS OF NEW 1-AROYLAMINO-3-SULFONYLPYRROLES BY REACTION OF AROYLAZOALKENES WITH 1,3-KETOSULFONES [J].
ATTANASI, OA ;
GROSSI, M ;
SERRAZANETTI, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (04) :1263-1264
[6]   CONJUGATED AZOALKENES .4. SYNTHESIS OF UNUSUAL CONJUGATED AZOALKENES [J].
ATTANASI, OA ;
GROSSI, M ;
MEI, A ;
SERRAZANETTI, F .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1988, 20 (04) :408-414
[7]   CONJUGATED AZOALKENES .9. NEW 1-AMINO-4-TRIPHENYLPHOSPHORANYLIDENE-5-OXO-2-PYRROLINES OR ALPHA,BETA-UNSATURATED HYDRAZONES BY REACTION OF AZOALKENES WITH CARBOALKOXYMETHYLENE TRIPHENYLPHOSPHORANE [J].
ATTANASI, OA ;
FILIPPONE, P ;
MEI, A ;
BONGINI, A ;
FORESTI, E .
TETRAHEDRON, 1990, 46 (16) :5685-5696
[8]   EFFECT OF METAL-IONS IN ORGANIC-SYNTHESIS .33. 2-HYDROXY-4-PYRROLINES AS STABLE INTERMEDIATES IN THE SYNTHESIS OF 1-AMINOPYRROLE DERIVATIVES [J].
ATTANASI, OA ;
GROSSI, M ;
SERRAZANETTI, F ;
FORESTI, E .
TETRAHEDRON, 1987, 43 (18) :4249-4256
[9]   CONJUGATED AZOALKENES .6. ALPHA-OLEFINATED CARBONYL DERIVATIVES BY TREATMENT OF AZOALKENES WITH CARBOMETHOXYMETHYLENE TRIPHENYLPHOSPHORANE [J].
ATTANASI, OA ;
FILIPPONE, P ;
SANTEUSANIO, S .
TETRAHEDRON LETTERS, 1988, 29 (45) :5787-5788
[10]   DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF CHIRAL 1,2-DIAZA-1,3-BUTADIENES DERIVED FROM CARBOHYDRATES [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
JIMENEZ, JL ;
MOLINA, MM ;
PALACIOS, JC ;
SANCHEZ, JB .
TETRAHEDRON LETTERS, 1991, 32 (22) :2513-2516