RETRO-COPE ELIMINATIONS IN THE SYNTHESIS OF 1,2,5-OXADIAZINANES FROM ALLYLAMINES AND NITRONES - A METHOD FOR THE AMINATION OF UNACTIVATED ALKENES

被引：38

作者：

GRAVESTOCK, MB

KNIGHT, DW

THORNTON, SR

机构：

[1] ICI AGROCHEM, JEALOTTS HILL RES STN, BRACKNELL RG12 3EY, BERKS, ENGLAND

[2] CHEM DEPT, NOTTINGHAM NG7 2RD, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 02期

关键词：

D O I：

10.1039/c39930000169

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heating an allylamine (e.g. 9) and a nitrone (e.g. 10) in an inert solvent produces often excellent yields of a 1,2,5-oxadiazinane (e.g. 11) by a pathway which features a retro-Cope elimination and a Meisenheimer rearrangement; reduction of the oxadiazinanes leads to vicinal diamines and hence overall amination of the alkene function in the original allylamine.

引用

页码：169 / 171

页数：3

共 22 条

[1] NITRONES AND OXAZIRIDINES .22. PREPARATION AND CYCLIZATION OF SOME DELTA,EPSILON-UNSATURATED HYDROXYLAMINES
BLACK, DSC
DOYLE, JE
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) : 2317 - 2322
[2] SYNTHESIS OF IMINOMETHANO-DIBENZO[A,E]CYCLOOCTENES BY TRANS-ANNULAR FORMATION AND CLEAVAGE OF ISOXAZOLIDINES
CARLING, RW
LEESON, PD
[J]. TETRAHEDRON LETTERS, 1988, 29 (52) : 6985 - 6988
[3] REVERSE COPE ELIMINATIONS - PYRROLIDINE AND PIPERIDINE N-OXIDES BY INTRAMOLECULAR ADDITION OF N,N-DISUBSTITUTED HYDROXYLAMINES TO UNACTIVATED DOUBLE-BONDS
CIGANEK, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3007 - 3009
[4] CLIZBE LA, 1978, ORG SYNTH, V58, P5
[5] HYDROXYLAMINE-ALKYNE CYCLIZATIONS - SYNTHESIS OF THE 7-MEMBERED LACTAM STRUCTURE PROPOSED FOR (+/-)-ACACIALACTAM
FOX, ME
HOLMES, AB
FORBES, IT
THOMPSON, M
ZILLER, JW
[J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7425 - 7428
[6] HYDROXYLAMINE-ALKYNE CYCLIZATIONS - A NEW METHOD FOR THE SYNTHESIS OF CYCLIC NITRONES
FOX, ME
HOLMES, AB
FORBES, IT
THOMPSON, M
[J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7421 - 7424
[7] GRAVESTOCK MB, UNPUB
[8] EFFECT OF STRUCTURE ON TANDEM 1,2-PROTOTROPY-CYCLOADDITION VERSUS TANDEM CYCLIZATION-CYCLOADDITION REACTIONS OF OXIMES
GRIGG, R
MARKANDU, J
PERRIOR, T
SURENDRAKUMAR, S
WARNOCK, WJ
[J]. TETRAHEDRON LETTERS, 1990, 31 (04) : 559 - 562
[9] X=Y - ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .35. GENERATION OF NITRONES FROM OXIMES - CLASS-3 PROCESSES - TANDEM INTRAMOLECULAR MICHAEL ADDITION (1,3-AZAPROTIO CYCLOTRANSFER) - INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS
GRIGG, R
MARKANDU, J
PERRIOR, T
SURENDRAKUMAR, S
WARNOCK, WJ
[J]. TETRAHEDRON, 1992, 48 (33) : 6929 - 6952
[10] STEREOSELECTIVE SYNTHESIS OF (+/-)-INDOLIZIDINES 167B, 205A, AND 207A - ENANTIOSELECTIVE SYNTHESIS OF (-)-INDOLIZIDINE 209B
HOLMES, AB
SMITH, AL
WILLIAMS, SF
HUGHES, LR
LIDERT, Z
SWITHENBANK, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) : 1393 - 1405

← 1 2 3 →