DBU/AgOTf Relay-Catalysis Enabled One-Pot Synthesis of 1,3-Dihydroisobenzofurans and Its Conversion to Indanones

被引:4
|
作者
Wang, Jiazhuang [1 ]
Huang, Hongtai [1 ]
Gao, Haotian [1 ]
Qin, Guiping [1 ]
Xiao, Tiebo [1 ]
Jiang, Yubo [1 ]
机构
[1] Kunming Univ Sci & Technol, Fac Sci, Kunming 650500, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
1,3-Dihydroisobenzofurans; Indanones; One-pot synthesis; 2-Alkynylbenzaldehyde; alpha-Diazo esters; O-ALKYNYL ACETOPHENONE; ALDOL-TYPE REACTION; C-H; CARBONYLATIVE CYCLIZATION; EFFICIENT SYNTHESIS; ARYL IODIDES; CASCADE; DERIVATIVES; REARRANGEMENT; INDENONES;
D O I
10.1002/adsc.202200287
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A DBU/AgOTf relay-catalyzed one-pot reaction of 2-alkynylbenzaldehydes and alpha-diazo esters for the efficient construction of 1,3-dihydroisobenzofuran derivatives has been documented. This protocol can tolerate a wide range of substrates and its scalability is demonstrated by the gram-scale reaction. Moreover, the obtained 1,3-dihydroisobenzofurans can be converted to indanone derivatives by a AgOTf-catalyzed ring recombination process. Both of the resulting products, 1,3-dihydroisobenzofurans and indanones, are important structural units of a variety of pharmaceuticals and natural products, and their structures are clearly confirmed by single crystal X-ray diffraction analysis.
引用
收藏
页码:1896 / 1902
页数:7
相关论文
共 50 条
  • [31] NOVEL ONE-POT SYNTHESIS OF 1-IODO-1-TRIMETHYLSILYL 1,3-DIENES
    SHEN, YC
    WANG, TL
    XIA, W
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03): : 389 - 391
  • [32] Novel one-pot synthesis of 1,3-dithiins and 1,3-thiazines under microwave irradiation
    Siddiqui, Ibadur R.
    Singh, Pravin K.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2007, 46 (03): : 499 - 504
  • [33] Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates
    Nimmagadda, Krishna
    Zhang, Zuhui
    Antilla, Jon C.
    ORGANIC LETTERS, 2014, 16 (16) : 4098 - 4101
  • [34] Asymmetric one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes via hemiaminal intermediates
    Nimmagadda, Sri Krishna
    Zhang, Zuhui
    Antilla, Jon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [35] SELENOSULFONATION OF 1,3-DIENES - ONE-POT SYNTHESIS OF 2-(PHENYLSULFONYL)-1,3-DIENES
    BACKVALL, JE
    NAJERA, C
    YUS, M
    TETRAHEDRON LETTERS, 1988, 29 (12) : 1445 - 1448
  • [36] Enzyme and photoredox sequential catalysis for the synthesis of 1,3-oxazine derivatives in one pot
    Zhang, Guo-Yan
    Xiang, Yang
    Guan, Zhi
    He, Yan-Hong
    CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (09) : 1937 - 1942
  • [37] DBU-MeOH promoted one-pot stereoselective γ-functionalization of 1,3-dicarbonyls:: Reactivity of β-ketoamides towards α,β-unsaturated aldehydes
    Charonnet, E
    Filippini, MH
    Rodriguez, J
    SYNLETT, 1999, (12) : 1951 - 1953
  • [38] One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis
    Landstrom, Evan B.
    Akporji, Nnamdi
    Lee, Nicholas R.
    Gabriel, Christopher M.
    Braga, Felipe C.
    Lipshutz, Bruce H.
    ORGANIC LETTERS, 2020, 22 (16) : 6543 - 6546
  • [39] AgOTf/Et3N Cooperative Catalysis Enabled One-Pot Access to α-(Indolizinylethyl)-Substituted N-Sulfonyl Ketimines via an Imino-Alkyne Cyclization
    Lodhi, Rajni
    Patel, Ashvani K. K.
    Samanta, Sampak
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)