[2,3] SIGMATROPIC REARRANGEMENT OF 1-VINYLIC TETRAHYDROISOQUINOLINE N-YLIDES AND N-OXIDES

被引：11

作者：

BAILEY, TS

BREMNER, JB

CARVER, JA

机构：

[1] UNIV TASMANIA,DEPT CHEM,GPO BOX 252C,HOBART,TAS 7001,AUSTRALIA

[2] UNIV WOLLONGONG,DEPT CHEM,WOLLONGONG,NSW 2500,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(00)73696-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[2.3] Sigmatropic rearrangement of the N-ylides from the 1-vinyl and 1-(1-propenyl) tetrahydroisoquinolinium salts 3a and 3b at room temperature in acetonitrile gave high yields of the functionalised 3-benzazonine derivatives 6a (90%: E/Z = 19) and 6b (93%: E/Z = 2) respectively. The N-oxide analogues 4a and 4b gave the 2.3-benzoxazepines 8a and 8b, together with the first representative of the 4,3-benzoxazonine system, 9b, from 4b.

引用

页码：3331 / 3334

页数：4

共 11 条

[1] BREMNER JB, 1990, STUDIES NATURAL PROD, V6, P467
[2] MEISENHEIMER REARRANGEMENT OF 2-ETHENYL-1,4,5,10B-TETRAHYDRO-2H-AZETOPYRIDO[3,4-B]INDOLE N-OXIDES - NEW ROUTE TO THE 12(S)CARBA-EUDISTOMIN SKELETON
KURIHARA, T
DOI, M
HAMAURA, K
OHISHI, H
HARUSAWA, S
YONEDA, R
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (03) : 811 - 813
[3] MEISENHEIMER REARRANGEMENT OF AZETOPYRIDOINDOLES .4. RING EXPANSION OF 2-VINYL-1,2,4,5,10,10B-HEXAHYDROAZETO[1',2'-1,2]PYRIDO[3,4-B]INDOLE N-OXIDES
KURIHARA, T
SAKAMOTO, Y
TSUKAMOTO, K
OHISHI, H
HARUSAWA, S
YONEDA, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01): : 81 - 87
[4] REARRANGEMENT OF CATHARANTHINE SKELETON
LANGLOIS, Y
GUERITTE, F
ANDRIAMIALISOA, RZ
LANGLOIS, N
POTIER, P
CHIARONI, A
RICHE, C
[J]. TETRAHEDRON, 1976, 32 (08) : 945 - 949
[5] Marko I. E., 1991, COMPREHENSIVE ORGANI, V3, P913
[6] STEREOCHEMISTRY IN A MEDIUM-SIZED RING - HIGHLY DIASTEREOSELECTIVE N-OXIDATION OF A SUBSTITUTED 3-BENZAZONINE - X-RAY CRYSTAL-STRUCTURE OF AN UNUSUAL COMPLEX BETWEEN AN AMINE N-OXIDE AND SACCHARIN
MARYANOFF, BE
PARVEZ, M
OLOFSON, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) : 760 - 764
[7] SASHIDA H, 1984, CHEM PHARM BULL, V32, P4117
[8] REARRANGEMENTS OF 1,6,7-TRISUBSTITUTED 2-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINIUM 2-METHYLIDES
SATO, Y
SHIRAI, N
MACHIDA, Y
ITO, E
YASUI, T
KURONO, Y
HATANO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) : 6711 - 6716
[9] SPATH E, 1926, CHEM BER, V59, P2791
[10] RING EXPANSION BY [2,3]SIGMATROPIC SHIFT - CONVERSION OF 5-MEMBERED INTO 8-MEMBERED HETEROCYCLES
VEDEJS, E
HAGEN, JP
ROACH, BL
SPEAR, KL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) : 1185 - 1190

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