Synthesis of diarylazepan-4-ones

被引：16

作者：

Chang, Meng-Yang ^{[1
]}

Kung, Yung-Hua ^{[1
]}

Ma, Chih-Chong ^{[1
]}

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 02期

关键词：

diarylazepan-4-ones; m-chloroperoxybenzoic acid; boron trifluoride etherate; Grignard addition/dehydration; epoxidation/pinacol rearrangement;

D O I：

10.1016/j.tetlet.2006.11.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic acid ethyl ester. The single isomer with the structural skeleton of 3,3-diarylazepan-4-one and 5,5-diarylazepan-4-one is constructed in two functional group transformations of Grignard addition/dehydration and epoxidation/pinacol rearrangement. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：199 / 202

页数：4

共 37 条

[1] Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome [J].

Barluenga, S ;

Simonsen, KB ;

Littlefield, ES ;

Ayida, BK ;

Vourloumis, D ;

Winters, GC ;

Takahashi, M ;

Shandrick, S ;

Zhao, Q ;

Han, Q ;

Hermann, T .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (03) :713-718

[2] GLYCINE ANTAGONISTS - SYNTHESIS, STRUCTURE, AND BIOLOGICAL EFFECTS OF SOME BICYCLIC 5-ISOXAZOLOL ZWITTERIONS [J].

BREHM, L ;

KROGSGAARDLARSEN, P ;

SCHAUMBURG, K ;

JOHANSEN, JS ;

FALCH, E ;

CURTIS, DR .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (02) :224-229

[3] Structure-based optimization of novel azepane derivatives as PKB inhibitors [J].

Breitenlechner, CB ;

Wegge, T ;

Berillon, L ;

Graul, K ;

Marzenell, M ;

Friebe, WG ;

Thomas, U ;

Schumacher, R ;

Huber, R ;

Engh, RA ;

Masjost, B .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (06) :1375-1390

[4] Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones [J].

Burtin, G ;

Corringer, PJ ;

Hitchcock, PB ;

Young, DW .

TETRAHEDRON LETTERS, 1999, 40 (22) :4275-4278

[5] Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids [J].

Burtin, G ;

Corringer, PJ ;

Young, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3451-3459

[6] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[7] Rescuing the traffic-deficient mutants of rat μ-opioid receptors with hydrophobic ligands [J].

Chaipatikul, V ;

Erickson-Herbrandson, LJ ;

Loh, HH ;

Law, PY .

MOLECULAR PHARMACOLOGY, 2003, 64 (01) :32-41

[8] CAN-mediated rearrangement of 4-benzhydrylidenepiperidines [J].

Chang, Meng-Yang ;

Wu, Tsun-Cheng ;

Lin, Chun-Yu ;

Hung, Ching-Yi .

TETRAHEDRON LETTERS, 2006, 47 (47) :8347-8350

[9] Synthesis of (2R,3S,4S)-4-aryl-3-hydroxyprolinols [J].

Chang, Meng-Yang ;

Lin, Chun-Yu ;

Wu, Tsun-Cheng .

TETRAHEDRON, 2006, 62 (52) :12334-12339

[10] New synthesis of SKF 89976A [J].

Chang, Meng-Yang ;

Wang, Si-Yun ;

Pai, Chun-Li .

TETRAHEDRON LETTERS, 2006, 47 (36) :6389-6392

← 1 2 3 4 →