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
来源：
HETEROCYCLES | 2013年 / 87卷 / 11期
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 50 条
  • [31] SYNTHESIS OF BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLE BY THE REACTION OF 2-AMINO-4,5-DIHYDRO-3-FURANCARBONITRILE AND o-SUBSTITUTED ANILINES IN THE CATALYSIS OF TRIMETYLAMINE HYDROCHLORIDE
    Okabe-Nakahara, Fumi
    Nagabuchi, Hayate
    Masumoto, Eiichi
    Maruoka, Hiroshi
    HETEROCYCLES, 2021, 102 (11) : 2207 - 2214
  • [32] Umpolung Strategy for the Synthesis of Chiral Dispiro[2-amino-4,5-dihydrofuran-3-carbonitrile]bisoxindoles
    Chen, Li-Jun
    Yu, Jin-Hang
    He, Bin
    Xie, Jian-Wu
    Liu, Yuan-Xiu
    Zhu, Wei-Dong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 7793 - 7802
  • [33] A convenient synthesis of polysubstituted 2-amino-4,5-dihydrofuran-3-nitriles from benzoins or benzaldehydes
    Du, Ding
    Hu, Zhongyuan
    Tang, Weifang
    Wang, Bo
    Lu, Tao
    TETRAHEDRON LETTERS, 2012, 53 (04) : 453 - 457
  • [34] Antiviral activity of 2-amino-4, 4a-dihydro-4a-7-dimethyl-3H-phenoxazine-3-one on poliovirus
    Iwata, A
    Yamaguchi, T
    Sato, K
    Izumi, R
    Tomoda, A
    TOHOKU JOURNAL OF EXPERIMENTAL MEDICINE, 2003, 200 (03): : 161 - 165
  • [35] Reversible 1,3-dipolar cycloaddition of dimethyl 2-thiono-1,3-dithiole-4,5-dicarboxylate with dimethyl acetylenedicarboxylate
    Nakayama, J
    Kaneko, A
    Sugihara, Y
    Ishii, A
    Oishi, A
    Shibuya, I
    HETEROATOM CHEMISTRY, 2000, 11 (06) : 434 - 440
  • [36] Synthesis of 2-amino-4,6-dimethoxypyrimidine with dimethyl carbonate as methylating agent
    Zhen Xiong
    Minghao Zhou
    Guomin Xiao
    Research on Chemical Intermediates, 2014, 40 : 1789 - 1797
  • [37] Base-catalyzed three-component synthesis of 2-amino-4,5-dihydro-4-arylpyrano[3,2-b]indole-3-carbonitriles
    Damavandi, Saman
    HETEROCYCLIC COMMUNICATIONS, 2011, 17 (3-4) : 125 - 127
  • [38] Synthesis of 2-amino-4,6-dimethoxypyrimidine with dimethyl carbonate as methylating agent
    Xiong, Zhen
    Zhou, Minghao
    Xiao, Guomin
    RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (05) : 1789 - 1797
  • [39] UNUSUAL REACTION OF DIMETHYL ACETYLENEDICARBOXYLATE WITH ETHYL 2-AMINO-3-THIOPHENECARBOXYLATE
    BIERE, H
    HERRMANN, C
    HOYER, GA
    CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (02): : 770 - 779
  • [40] CYCLIZATION OF NITRILES .1. THE SYNTHESIS OF 2-AMINO-4,5-DIARYLOXAZOLES AND DIHETERYLOXAZOLES
    SHARANIN, YA
    ZHURNAL ORGANICHESKOI KHIMII, 1980, 16 (10): : 2185 - 2188
12345