SYNTHESIS OF DIHYDROOXEPINS BY THE CYCLOADDITION OF 2-AMINO-4,5-DIHYDRO-3-FURANCARBONITRILES WITH DIMETHYL ACETYLENEDICARBOXYLATE

被引:0
作者
Okabe, Fumi [1 ]
Maruoka, Hiroshi [1 ]
Masumoto, Eiichi [1 ]
Fujioka, Toshihiro [1 ]
Yamagata, Kenji [1 ]
机构
[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, Fukuoka 8140180, Japan
关键词
BETA-ENAMINO ESTERS; HETEROCYCLIC ENAMINONITRILES; STRUCTURAL ELUCIDATION; CIGUATOXIN; TRITERPENOIDS; ZOAPATANOL; CHEMISTRY; SPONGE;
D O I
10.3987/COM-13-12819
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient synthesis of dihydrooxepins is described. Treatment of readily available 2-amino-4,5-dihydro-3-furancarbonitriles with dimethyl acetylenedicarboxylate at room temperature caused smoothly a cycloaddition reaction, followed by a ring expansion, giving the corresponding dihydrooxepin derivatives.
引用
收藏
页码:2361 / 2368
页数:8
相关论文
共 39 条
  • [1] Belen'kll L. I., 1996, COMPREHENSIVE HETERO, V9, P45
  • [2] REACTION OF ENAMINES OF CYCLIC KETONES WITH DIMETHYL ACETYLENEDICARBOXYLATE
    BERCHTOLD, GA
    UHLIG, GF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) : 1459 - &
  • [3] ENAMINE CHEMISTRY .2. REACTIONS WITH ACETYLENEDICARBOXYLATES
    BRANNOCK, KC
    BURPITT, RD
    THWEATT, JG
    GOODLETT, VW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) : 1464 - &
  • [4] Bremner JB, 2005, PROG HET CH, V17, P389, DOI 10.1016/S0959-6380(05)80338-1
  • [5] Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference
    Candenas, ML
    Pinto, FM
    Cintado, CG
    Morales, EQ
    Brouard, I
    Díaz, MT
    Rico, M
    Rodríguez, E
    Rodríguez, RM
    Pérez, R
    Pérez, RL
    Martín, JD
    [J]. TETRAHEDRON, 2002, 58 (10) : 1921 - 1942
  • [6] MINOR TRITERPENOIDS FROM THE MEDITERRANEAN SPONGE, RASPACIONA-ACULEATA
    CIMINO, G
    MADAIO, A
    TRIVELLONE, E
    URIZ, M
    [J]. JOURNAL OF NATURAL PRODUCTS, 1994, 57 (06): : 784 - 790
  • [7] METHOXYTETRAHYDROPYRANS - A NEW SERIES OF SELECTIVE AND ORALLY POTENT 5-LIPOXYGENASE INHIBITORS
    CRAWLEY, GC
    DOWELL, RI
    EDWARDS, PN
    FOSTER, SJ
    MCMILLAN, RM
    WALKER, ERH
    WATERSON, D
    BIRD, TGC
    BRUNEAU, P
    GIRODEAU, JM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) : 2600 - 2609
  • [8] Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines
    Edrada, RA
    Proksch, P
    Wray, V
    Witte, L
    van Ofwegen, LP
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (03): : 358 - 361
  • [9] Saturated oxygen heterocycles
    Elliott, MC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (21): : 2301 - 2323
  • [10] Saturated oxygen heterocycles
    Elliott, MC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09): : 1291 - 1318