Cleavage of the N(1)-C(4) bond of 4-(4′-hydroxyphenyl)-azetidine-2-ones via quinone methide intermediates

被引：6

作者：

Cabell, LA ^{[1
]}

Hedrich, LW ^{[1
]}

McMurray, JS ^{[1
]}

机构：

[1] Univ Texas, MD Anderson Canc Ctr, Dept Neurooncol, Houston, TX 77030 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 48期

关键词：

beta-lactam; quinone methide; 1,6 conjugate addition;

D O I：

10.1016/S0040-4039(01)01849-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper we describe a novel ring-opening reaction in which 4-(4'-hydroxyphenyl)-azetidine-2-ones, on treatment with base, rearrange to quinone methide intermediates with concomitant cleavage of the C(4)-N(1) bond. The quinone methide intermediate serves as a substrate for Michael-type 1,6 conjugate additions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8409 / 8413

页数：5

共 39 条

[1] Stereoselective synthesis of 3-substituted 4-(formyloxy)-2-azetidinones by the unusual Baeyer-Villiger reaction of beta-lactam aldehydes. Scope and synthetic applications
Alcaide, B
Aly, MF
Sierra, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8819 - 8825
[2] A NOVEL FRAGMENTATION OF THE BETA-LACTAM RING - STEREOSELECTIVE ENTRY TO VINYL ETHERS BY REACTION OF N-(ARYLIDENE(OR ALKYLIDENE)AMINO)-2-AZETIDINONES WITH OZONE
ALCAIDE, B
MIRANDA, M
PEREZCASTELLS, J
SIERRA, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 297 - 298
[3] NEW REACTIVITY PATTERNS OF THE BETA-LACTAM RING - TANDEM C3-C4 BOND BREAKAGE REARRANGEMENT OF 4-ACYL-3,3-DIMETHOXY-2-AZETIDINONES OR 4-IMINO-3,3-DIMETHOXY-2-AZETIDINONES PROMOTED BY SNCL2.2H2O
ALCAIDE, B
MARTINCANTALEJO, Y
RODRIGUEZLOPEZ, J
SIERRA, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4767 - 4770
[4] The asymmetric synthesis of 2,3-benzocarbapenems by intramolecular aryl radical cyclizations
Alcaide, B
Moreno, AM
RodriguezVicente, A
Sierra, MA
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2203 - 2206
[5] Stereoselective synthesis of 2-azetidinones as cholesterol-absorption inhibitors
Annunziata, R
Benaglia, M
Cinquini, M
Cozzi, F
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (24) : 4841 - 4849
[6] Microwave-induced organic reaction enhancement (MORE) chemistry. Part 13. Microwave-assisted rapid and simplified hydrogenation
Banik, BK
Barakat, KJ
Wagle, DR
Manhas, MS
Bose, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 5746 - 5753
[7] Simple and condensed β-lactams -: Part 31.: Acid catalyzed ring closures and ring transformations of some 3-aryloxy-4-oxoazetidin-2-carbaldehydes
Bertha, F
Fetter, J
Kajtár-Peredy, M
Lempert, K
Czira, G
[J]. TETRAHEDRON, 1998, 54 (50) : 15227 - 15242
[8] Simple and condensed β-lactams.: Part 33.: AlCl3 catalyzed ring closures of some 3-aryloxy-4-oxoazetidine-2-carboxylic chlorides to 1H-chromeno[3,2-b]azete-2,8(2aH,8aH)-diones and some reactions of the products
Bertha, F
Fetter, J
Kajtár-Peredy, M
Lempert, K
[J]. TETRAHEDRON, 1999, 55 (17) : 5567 - 5580
[9] Boge T C., 1997, ENANTIOSELECTIVE SYN, P1
[10] Design and synthesis of monocyclic β-lactams as mechanism-based inhibitors of human cytomegalovirus protease.
Borthwick, AD
Weingarten, G
Haley, TM
Tomaszewski, M
Wang, W
Hu, ZH
Bedard, J
Jin, HL
Yuen, L
Mansour, TS
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (04) : 365 - 370

← 1 2 3 4 →