Multicomponent synthesis of spiroisoxazolines

被引:72
作者
Adamo, MFA
Donati, D
Duffy, EF
Sarti-Fantoni, P
机构
[1] Royal Coll Surgeons Ireland, Ctr Synth & Chem Biol, Dept Pharmaceut & Med Chem, Dublin 2, Ireland
[2] Univ Siena, Dipartimento Chim, I-53100 Siena, Italy
[3] Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy
关键词
D O I
10.1021/jo051181w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component one-pot procedure (3-MCR) was developed to assemble the spiroisoxazoline nucleus from commercially available materials. This new methodology affords the title compounds in high yields and without the use of chromatography.
引用
收藏
页码:8395 / 8399
页数:5
相关论文
共 28 条
[1]   Application of bis-acetylenic ketones in synthesis: One-pot preparation of the 1,2,4-triazepine and oxatriazaindenone cores [J].
Adamo, MFA ;
Baldwin, JE ;
Adlington, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3307-3308
[2]   Practical routes to diacetylenic ketones and their application for the preparation of alkynyl substituted pyridines, pyrimidines and pyrazoles [J].
Adamo, MFA ;
Adlington, RM ;
Baldwin, JE ;
Pritchard, GJ ;
Rathmell, RE .
TETRAHEDRON, 2003, 59 (13) :2197-2205
[3]   Triethylammonium 8-acetyl-3-methyl-9-phenyl-7-oxo-2-azaspiro[4.5]dec-2-ene-4-nitronate [J].
Adamo, MFA ;
Chimichi, S ;
Donati, D ;
Sarti-Fantoni, P .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 :O1125-O1127
[4]   The reactivity of 3-methyl-4-nitro-5-styrylisoxazole with some bis-enolisable ketones [J].
Adamo, MFA ;
Chimichi, S ;
De Sio, F ;
Donati, D ;
Sarti-Fantoni, P .
TETRAHEDRON LETTERS, 2002, 43 (23) :4157-4160
[5]   PREPARATION OF O-18-BILABELED CARBOXYLIC-ACIDS - CINNAMIC AND PHENYLPROPIOLIC ACIDS VIA STYRYLISOXAZOLES [J].
BARACCHI, A ;
CHIMICHI, S ;
DESIO, F ;
DONATI, D ;
NESI, R ;
SARTIFANTONI, P ;
TORROBA, T .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1986, 23 (05) :487-493
[6]  
BARACCHI A, 1986, HETEROCYCLES, V24, P2863
[7]   A nonpeptide integrin antagonist can inhibit epithelial cell ingestion of Streptococcus pyogenes by blocking formation of integrin α5β1-fibronectin-M1 protein complexes [J].
Cue, D ;
Southern, SO ;
Southern, PJ ;
Prabhakar, J ;
Lorelli, W ;
Smallheer, JM ;
Mousa, SA ;
Cleary, PP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (06) :2858-2863
[8]   NITRILE OXIDES IN MEDICINAL CHEMISTRY .2. SYNTHESIS OF THE 2 ENANTIOMERS OF DIHYDROMUSCIMOL [J].
DEAMICI, M ;
DEMICHELI, C ;
MISANI, V .
TETRAHEDRON, 1990, 46 (06) :1975-1986
[9]   PHOTODIMERIZATION OF 3-METHYL-4-NITRO-5-STYRYLISOXAZOLE IN SOLID-STATE [J].
DONATI, D ;
FIORENZA, M ;
MOSCHI, E ;
SARTIFANTONI, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (05) :951-951
[10]   Aerothionin, a bromotyrosine derivative with antimycobacterial activity from the marine sponge Aplysina gerardogreeni (Demospongia) [J].
Encarnación-Dimayuga, R ;
Ramírez, MR ;
Luna-Herrera, J .
PHARMACEUTICAL BIOLOGY, 2003, 41 (05) :384-387