One-Pot Synthesis of Decahydropyrene via Tandem C-H Activation/Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition

被引:13
|
作者
Lin, Hui [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
关键词
INTERNAL ALKYNES; POLYHETEROAROMATIC COMPOUNDS; CATALYZED ANNULATION; CARBOXYLIC-ACIDS; DIRECTING GROUPS; BOND ACTIVATION; N-OXIDES; HYDROGENATION; BENZAMIDES; ARYLATION;
D O I
10.1021/acs.orglett.6b02768
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C-H activation/intramolecular Diels-Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.
引用
收藏
页码:5524 / 5527
页数:4
相关论文
共 50 条
  • [1] Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles
    Wilkie, GD
    Elliott, GI
    Blagg, BSJ
    Wolkenberg, SE
    Soenen, DR
    Miller, MM
    Pollack, S
    Boger, DL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) : 11292 - 11294
  • [2] 1,3-DIPOLAR AND DIELS-ALDER CYCLOADDITION REACTIVITY OF LUMISANTONIN
    SASAKI, T
    EGUCHI, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (12): : 4389 - &
  • [3] Diastereoselective Synthesis of Coumarin-Based Fused Heterocycles via Intramolecular Diels-Alder and 1,3-Dipolar Cycloaddition Reactions
    Alizadeh, Abdolali
    Farajpour, Behnaz
    Amir Ashjaee Asalemi, Kaveh
    Taghipour, Sajad
    [J]. CHEMISTRYSELECT, 2020, 5 (31): : 9834 - 9838
  • [4] Total synthesis of (-)- and ent-(+)-vindorosine:: Tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles
    Elliott, GI
    Velcicky, J
    Ishikawa, H
    Li, YK
    Boger, DL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (04) : 620 - 622
  • [5] DOUBLE CYCLOADDITION REACTION OF IMIDAZOLIUM METHYLIDES - INTERMOLECULAR 1,3-DIPOLAR AND INTRAMOLECULAR DIELS-ALDER CYCLOADDITION REACTIONS
    TSUGE, O
    KANEMASA, S
    TAKENAKA, S
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (07) : 2073 - 2076
  • [6] Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications
    Sears, Justin E.
    Boger, Dale L.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (02) : 241 - 251
  • [7] Conformational preferences of methacrolein in Diels-Alder and 1,3-dipolar cycloaddition reactions
    Barba, Carmen
    Carmona, Daniel
    Garcia, Jose Ignacio
    Lamata, Maria Pilar
    Mayoral, Jose Antonio
    Salvatella, Luis
    Viguri, Fernando
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9831 - 9840
  • [8] ONE-POT SYNTHESIS OF N-ALKYLPYRROLIDINES BY 1,3-DIPOLAR CYCLOADDITION
    IMAI, N
    ACHIWA, K
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (02) : 593 - 601
  • [9] Tandem inverse electron demand Diels-Alder, retro-Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles
    Bromley, William J.
    Gibson, Mairi
    Lang, Stuart
    Raw, Steven A.
    Whitwood, Adrian C.
    Taylor, Richard J. K.
    [J]. TETRAHEDRON, 2007, 63 (26) : 6004 - 6014
  • [10] SEQUENTIAL INTRAMOLECULAR DIELS-ALDER REACTION AND INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTION - ONE-POT [6.6.5]ANNELATION REACTION LEADING TO THE FORMATION OF POLYAZA-STEROID TYPE SKELETONS
    TSUGE, O
    UENO, K
    KANEMASA, S
    [J]. HETEROCYCLES, 1986, 24 (03) : 629 - 632