The stereochemistry of organometallic compounds .43. Rhodium-catalysed reactions of 2-(alkenyloxy)benzylamines and 2-(N-allyl-N-benzylamino)benzylamine

被引：26

作者：

Campi, EM ^{[1
]}

Jackson, WR ^{[1
]}

McCubbin, QJ ^{[1
]}

Trnacek, AE ^{[1
]}

机构：

[1] MONASH UNIV,DEPT CHEM,CLAYTON,VIC 3168,AUSTRALIA

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1996年 / 49卷 / 02期

关键词：

D O I：

10.1071/CH9960219

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of 2-(allyloxy)benzylamines with H-2/CO in the presence of rhodium catalysts give 1,3-benzoxazines, and 2-(N-allyl-N-benzylamino)benzylamine gives a quinazoline. These reactions have been shown to involve allylic cleavage followed by regioselective carbonylation at the internal carbon atom as demonstrated by crossover experiments. Reactions of longer chain (alkenyloxy)benzylamines under similar conditions give polymeric material.

引用

页码：219 / 230

页数：12

共 23 条

[1] REDUCTION OF NITRILES TO PRIMARY AMINES WITH LITHIUM ALUMINUM HYDRIDE
AMUNDSEN, LH
NELSON, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) : 242 - 244
[2] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .35. HYDROFORMYLATION OF ORTHO-PROPENYLANILINES AND ORTHO-PROPENYLPHENOLS - A NEW ROUTE TO 4,5-DIHYDRO-3H-1-BENZAZEPINES
ANASTASIOU, D
JACKSON, WR
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (01) : 21 - 37
[3] SYNTHESIS OF 2,3,5,6-TETRAHYDROIMIDAZO[1,2-C]QUINAZOLINE DERIVATIVES AS POTENTIAL NARCOTIC-ANTAGONISTS
ANTONINI, I
CRISTALLI, G
FRANCHETTI, P
GRIFANTINI, M
MARTELLI, S
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (01) : 155 - 157
[4] BLAIZE MW, 1994, INORG CHIM ACTA, V223, P1
[5] ALLYLIC REARRANGEMENTS DURING THE RHODIUM-CATALYZED REACTIONS OF 2-ALLYLOXYBENZYLAMINES AND 2-(N-ALLYL-N-BENZYLAMINO)BENZYLAMINE
CAMPI, EM
JACKSON, WR
MCCUBBIN, QJ
TRNACEK, AE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (24) : 2763 - 2763
[6] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .61. THE PREPARATION OF QUINAZOLINES AND QUINAZOLINONES INVOLVING RHODIUM-CATALYZED HYDROFORMYLATION OF ALKENYL ANILINES
CAMPI, EM
JACKSON, WR
MCCUBBIN, QJ
TRNACEK, AE
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (06) : 1061 - 1070
[7] The stereochemistry of organometallic compounds .42. The preparation of [2,1-b]quinazolines involving rhodium-catalysed hydroformylation of 2-amino-N-alkenylbenzylamines
Campi, EM
Habsuda, J
Jackson, WR
Jonasson, CAM
McCubbin, QJ
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (12) : 2023 - 2033
[8] DONOVAN RD, 1994, 208 AM CHEM SOC NATL
[9] ISOMERIZATION OF ALDOXIMES TO AMIDES UNDER SUBSTANTIALLY NEUTRAL CONDITIONS
FIELD, L
MARSHALL, WS
SHUMAKER, SH
HUGHMARK, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (08) : 1983 - &
[10] HYDROFORMYLATION OF BISOLEFINIC AMINE DERIVATIVES CATALYZED BY COBALT AND RHODIUM
GARST, ME
LUKTON, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) : 4433 - 4438

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