Multicomponent synthesis of dihydrobenzoxazepinones by coupling Ugi and Mitsunobu reactions

被引:34
作者
Banfi, Luca [1 ]
Basso, Andrea [1 ]
Guanti, Giuseppe [1 ]
Lecinska, Paulina [1 ]
Riva, Renata [1 ]
机构
[1] Dept Chem & Ind Chem, I-16146 Genoa, Italy
关键词
D O I
10.1039/b613056a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various dihydrobenzo[f][1,4]oxazepin-5-ones have been convergently prepared in 2-3 steps by coupling Ugi and Mitsunobu reactions. Two alternative methodologies were used: in the first one the Ugi condensation was followed by a Mitsunobu cyclization (2 steps); in the second one an intermolecular Mitsunobu reaction was followed by a deprotection step and then by an intramolecular Ugi reaction. Also a "convertible" isocyanide was used.
引用
收藏
页码:4236 / 4240
页数:5
相关论文
共 19 条
  • [1] ANTHOINEDIETRIC.S, 2005, ORG BIOMOL CHEM, V3, P97
  • [2] Enantio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines through a multicomponent Ugi reaction and their transformation into bicyclic scaffolds
    Banfi, L
    Basso, A
    Guanti, G
    Riva, R
    [J]. TETRAHEDRON LETTERS, 2004, 45 (35) : 6637 - 6640
  • [3] Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams
    Banfi, L
    Basso, A
    Guanti, G
    Riva, R
    [J]. TETRAHEDRON LETTERS, 2003, 44 (41) : 7655 - 7658
  • [4] Banfi L., 2005, ORG REACTIONS, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
  • [5] A new highly convergent entry to densely functionalized aziridines based on the Ugi reaction
    Banfi, Luca
    Basso, Andrea
    Guanti, Giuseppe
    Paravidino, Monica
    Riva, Renata
    [J]. QSAR & COMBINATORIAL SCIENCE, 2006, 25 (5-6): : 457 - 460
  • [6] Preparation of optically pure fused polycyclic scaffolds by Ugi reaction followed by olefin and enyne metathesis
    Basso, Andrea
    Banfi, Luca
    Riva, Renata
    Guanti, Giuseppe
    [J]. TETRAHEDRON, 2006, 62 (37) : 8830 - 8837
  • [7] Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
  • [8] 2-A
  • [9] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [10] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO