A novel synthesis of tricyclic-fused hydrindene-azetidinone compounds by sequential Mn(III)-promoted 4-exo-trig cyclization/radical aromatic substitution

被引:20
作者
Cerreti, A [1 ]
D'Annibale, A [1 ]
Trogolo, C [1 ]
Umani, F [1 ]
机构
[1] Univ Rome La Sapienza, Dipartimento Chim, CNR, Ctr Studio Chim Sostanze Organ Nat, I-00185 Rome, Italy
关键词
cyclization; azetidinones; manganese and compounds; radicals and radical reaction; polycyclic heterocyclic compounds;
D O I
10.1016/S0040-4039(00)00364-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 2-acyl-N-(2,2-diphenyl-1-ethenyl)-N-alkylacetamides reacted with excess Mn(III) affording tricyclic fused hydrindene-azetidinones in good yields, through a 4-exo-trig radical cyclization process, and further ring closure of the azetidinone via radical aromatic substitution. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3261 / 3264
页数:4
相关论文
共 12 条
[1]   Mn(III)-promoted sulfur-directed 4-exo-trig radical cyclization of enamides to β-lactams [J].
Attenni, B ;
Cerreti, A ;
D'Annibale, A ;
Resta, S ;
Trogolo, C .
TETRAHEDRON, 1998, 54 (39) :12029-12038
[2]   β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations.: A concise construction of the mesembrine skeleton [J].
Cassayre, J ;
Quiclet-Sire, B ;
Saunier, JB ;
Zard, SZ .
TETRAHEDRON, 1998, 54 (07) :1029-1040
[3]   Diastereoselectivity in Mn(III)-promoted 4-exo-trig cyclization of enamides to β-lactams [J].
D'Annibale, A ;
Nanni, D ;
Trogolo, C ;
Umani, F .
ORGANIC LETTERS, 2000, 2 (03) :401-402
[4]   Manganese(III)-promoted free radical cyclizations of enamides leading to beta-lactams [J].
DAnnibale, A ;
Pesce, A ;
Resta, S ;
Trogolo, C .
TETRAHEDRON, 1997, 53 (38) :13129-13138
[5]   MN(III) - PROMOTED CYCLIZATION OF ENAMIDES - AN OXIDATIVE RADICAL APPROACH TO BETA-LACTAMS [J].
DANNIBALE, A ;
RESTA, S ;
TROGOLO, C .
TETRAHEDRON LETTERS, 1995, 36 (49) :9039-9042
[6]   Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides. [J].
DAnnibale, A ;
Pesce, A ;
Resta, S ;
Trogolo, C .
TETRAHEDRON LETTERS, 1996, 37 (41) :7429-7432
[7]   beta-lactams by a nickel powder acetic acid mediated radical cyclisation [J].
QuicletSire, B ;
Saunier, JB ;
Zard, SZ .
TETRAHEDRON LETTERS, 1996, 37 (09) :1397-1400
[8]  
SATO M, 1983, CHEM PHARM BULL, V31, P1896
[9]   MECHANISM OF MANGANESE(III)-BASED OXIDATION OF BETA-KETO-ESTERS [J].
SNIDER, BB ;
PATRICIA, JJ ;
KATES, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2137-2143
[10]   INTRAMOLECULAR REACTIONS OF N-ACYLIMINIUM INTERMEDIATES [J].
SPECKAMP, WN ;
HIEMSTRA, H .
TETRAHEDRON, 1985, 41 (20) :4367-4416