Lewis acid-mediated cyclizations of (2′-amino-N′-tert-butoxycarbonylbenzylidene)-3-alkenylamines

被引：26

作者：

Frank, KE ^{[1
]}

Aubé, J ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 40期

关键词：

D O I：

10.1016/S0040-4039(98)01596-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Depending on the method of activation, (2'-amino-N'-tert-butoxycarbonyl-benzylidene)-3-alkenylamines (1) react with Lewis acids (TiCl4 or TMSOTf) to afford either a novel Boc-assisted iminium ion formation/trapping sequence (giving hexahydropyrido[1,2-c]quinazolin-6-ones (2) or tetrahydropyrrolo[1,2-c]quinazolin-5-ones (4)) or a pseudodimerization process (leading to iminodibenzo[b,f]diazocines (3)). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7239 / 7242

页数：4

共 15 条

[1] STRUCTURES OF ANHYDRO-POLYMERS OF 2-AMINOBENZALDEHYDE
ALBERT, A
YAMAOTO, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (10): : 956 - &
[2] METAL TEMPLATE REACTIONS .4. ATTEMPTED DIMERIZATION OF ALPHA,OMEGA AMINO ALDEHYDES AROUND NICKEL(II) IONS
BLACK, DSC
LANE, MJ
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (10) : 2055 - &
[3] CROCE PD, 1988, J CHEM RES S, P346
[4] BIOMIMETIC POLYENE CYCLIZATIONS - ASYMMETRIC INDUCTION DURING THE ACID-CATALYZED CYCLIZATION OF CHIRAL IMINES
DEMAILLY, G
SOLLADIE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) : 3102 - 3108
[5] SILICON DIRECTED N-ACYLIMINIUM ION CYCLIZATIONS - HIGHLY SELECTIVE SYNTHESES OF (+/-)-ISORETRONECANOL AND (+/-)-EPILUPININE
HIEMSTRA, H
SNO, MHAM
VIJN, RJ
SPECKAMP, WN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) : 4014 - 4020
[6] ANALOGS OF 3-AMINO-7-CHLORO-1,2,4-BENZOTRIAZINE 1-OXIDE AS ANTIMALARIAL AGENTS
HORNER, JK
HENRY, DW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (05) : 946 - &
[7] Synthesis and x-ray crystallographic study of 6,12-epiiminodibenzo[b,f][1,5]diazocines
Molina, P
Arques, A
Tárraga, A
Obón, MD
Foces-Foces, C
Jagerovic, N
Elguero, J
[J]. TETRAHEDRON, 1998, 54 (5-6) : 997 - 1004
[8] THE STAUDINGER REACTION OF ORTHO-AZIDOBENZALDEHYDE WITH TRIPHENYLPHOSPHINE REVISITED - INFLUENCE OF THE TEMPERATURE ON THE NATURE OF THE REACTION-PRODUCTS
MOLINA, P
ARQUES, A
CARTAGENA, I
OBON, R
[J]. TETRAHEDRON LETTERS, 1991, 32 (22) : 2521 - 2524
[9] ORTHO FUNCTIONALIZATION OF N-(TERT-BUTOXYCARBONYL)ANILINE
MUCHOWSKI, JM
VENUTI, MC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) : 4798 - 4801
[10] CHARGE AS A KEY COMPONENT IN REACTION DESIGN - THE INVENTION OF CATIONIC CYCLIZATION REACTIONS OF IMPORTANCE IN SYNTHESIS
OVERMAN, LE
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (08) : 352 - 359

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