Ac2O-Mediated Dearylacetylative Dimerization of 2-Arylacetyl-1-naphthols: Synthesis of Naphtho[1,2-b]furan-3-ones

被引：7
|
作者：
Chang, Meng-Yang [1 ]
Chen, Kuan-Ting [1 ]
Hsiao, Yu-Ting [1 ]
Chen, Shin-Mei [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期
关键词：
PHOTO-FRIES REARRANGEMENTS; REACTIVITY; NAPHTHOLS;
D O I：
10.1021/acs.joc.9b03298
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient route for the synthesis of 2aryl-2-naphthyl naphtho[1,2-b]furan-3-ones is described via NaH/Ac2O-mediated dearylacetylative dimerization of 2-arylacetyl-1-naphthols in refluxing THF under open-flask conditions. A plausible mechanism is also proposed and discussed. Various reaction conditions are investigated for one-pot transformation.
引用
收藏
页码：3605 / 3616
页数：12
相关论文
共 50 条
  • [41] Synthesis　and　Crystal　Structure　of　3，3－Diphenylnaphtho　［1，2－b］furan－2（3H）－one
    Meng Ji-Ben
    Wen Zhong
    Wang Yong-Mei
    Wang Ru-Ji
    Wang Hong-Gen (Department of Chemistry and Central Laboratory
    结构化学, 1994, (02) : 99 - 101
  • [42] STUDIES IN IMIDAZOLE SERIES .75. SYNTHESIS OF 2-METHYLMERCAPTO-3-ACYL-METHYL(BETA-OXYALKYL)NAPHTHO[1,2-D]IMIDAZOLES AND THEIR TRANSFORMATIONS INTO DERIVATIVES OF NAPHTHO[1,2-D]IMIDAZO[3,2-B]IMIDAZOLE AND NAPHTHO[1,2-D]IMIDAZO[3,2-B]IMIDAZOLINE
    POVSTYANOI, MV
    KOCHERGI.PM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1972, (06): : 816 - +
  • [43] A method for the synthesis of 3a-aryl-substituted cyclopenta[1,2-b]furan derivatives
    Nemoto, H
    Peng, MA
    Zhong, WH
    Xie, J
    Kawamura, T
    Nishida, M
    SYNLETT, 2005, (20) : 3103 - 3106
  • [44] First asymmetric synthesis of 3-alkoxycarbonyl-2-amino-4-aryl-4H-naphtho[1,2-b]pyrans
    Martin, N
    MartinezGrau, A
    Seoane, C
    Marco, JL
    Albert, A
    Cano, FH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (01) : 27 - 31
  • [45] 2-allyl-N-benzyl substituted α-naphthylamines as building blocks in heterocyclic synthesis.: New and efficient syntheses of benz[e]naphtho[1,2-b]azepine and naphtho[1,2-b]azepine derivatives
    Yepez, Andres Felipe
    Palma, Alirio
    Stashenko, Elena
    Bahsas, Ali
    Amaro-Luis, Juan M.
    TETRAHEDRON LETTERS, 2006, 47 (32) : 5825 - 5828
  • [46] OXIDATION AND REDUCTION OF 5-HYDROXY-2-METHYLNAPHTHO[1,2-B]FURAN
    CAMERON, DW
    HILDYARD, EM
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (21): : 2126 - &
  • [47] Synthesis of 4H-naphtho [1,2-b]pyrans, benzo[h] coumarins, 4H-naphtho[2,1-b:6,5-b]dipyrans, 4H-naphtho[1,2-b:3,4-b'] dipyrans and pyridine derivatives
    ElTaweel, FMA
    Ayyad, SEN
    Elagamey, AGA
    Sowellim, SZA
    ANALES DE QUIMICA, 1995, 91 (7-8): : 589 - 593
  • [48] SYNTHESIS OF IMIDAZO[1,2-B][1,2]BENZOTHIAZINE-6,6-DIOXIDES AND PYRIMIDO[1,2-B][1,2]BENZOTHIAZINE-6,6-DIOXIDES
    RAJAGOPAL, R
    BHATIA, SI
    SESHADRI, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1991, 30 (07): : 655 - 657
  • [49] SYNTHESIS AND REACTIONS OF BUTYL 2-OXO-2H-NAPHTHO[1,2-B]PYRAN-4-ACETATE AND BUTYL 3-OXO-3H-NAPHTHO[2,1-B]PYRAN-1-ACETATE
    ELNAGDY, S
    SOLIMAN, AY
    ELBASSIOUNY, FAA
    BAKEER, HM
    MOUSTAFA, MM
    ACTA CHIMICA HUNGARICA-MODELS IN CHEMISTRY, 1991, 128 (01): : 35 - 40
  • [50] Photochromism of 2H-naphtho[1,2-b]pyran-4-carboxylates
    Graca, Vania
    Berthet, Jerome
    Delbaere, Stephanie
    Coelho, Paulo J.
    DYES AND PIGMENTS, 2023, 212
12345