Development of a Dual Fries-Claisen Rearrangement Strategy

被引：6
作者：
Duffy, Liam J. [2 ]
Garcia-Torres, Jason [3 ]
Jones, Raymond C. F. [3 ]
Allin, Steven M. [1 ]
机构：
[1] Nottingham Trent Univ, Sch Sci & Technol, Nottingham NG11 8NS, England
[2] Keele Univ, Res Inst Environm Phys Sci & Math, Keele ST5 5BG, Staffs, England
[3] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
来源：
SYNLETT | 2012年 / 12期
基金：
英国工程与自然科学研究理事会;
关键词：
annelation; pericyclic reaction; rearrangement; Fries; Claisen; RING-CLOSING METATHESIS; ANTHRACYCLINONES; DERIVATIVES; ROUTE;
D O I：
10.1055/s-0031-1291158
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper we describe the development and application of a sequential Fries-Claisen rearrangement strategy as a new route for annelation on an aromatic ring. We demonstrate the potential utility of this protocol through the synthesis of a pyranonaphtho-quinone target.
引用
收藏
页码：1821 / 1823
页数：3
相关论文
共 16 条
  • [1] Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases
    Assimomytis, Nikos
    Sariyannis, Yiannis
    Stavropoulos, Georgios
    Tsoungas, Petros G.
    Varvounis, George
    Cordopatis, Paul
    [J]. SYNLETT, 2009, (17) : 2777 - 2782
  • [2] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .21. CLAISEN REARRANGEMENTS OF SOME MIXED ALLYL ETHERS
    BEAUREGARD, DA
    CAMBIE, RC
    HIGGS, KC
    RUTLEDGE, PS
    WOODGATE, PD
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (07) : 1321 - 1333
  • [3] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .5. DOUBLE CLAISEN REARRANGEMENT OF 1,4-BIS(ALLYLOXY)ANTHRAQUINONES
    CAMBIE, RC
    ZHENDONG, H
    NOALL, WI
    RUTLEDGE, PS
    WOODGATE, PD
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) : 819 - 828
  • [4] Sequential double Claisen rearrangement and two-directional ring-closing metathesis as a route to various benzofused bisoxepin and bisoxocin derivatives
    Chattopadhyay, Shital K.
    Biswas, Titas
    Maity, Susama
    [J]. SYNLETT, 2006, (14) : 2211 - 2214
  • [5] CLAISEN AND FRIES REARRANGEMENT STUDIES OF SOME NAPHTHALENE DERIVATIVES
    GREEN, IR
    NEFDT, S
    HUGO, VI
    SNIJMAN, PW
    [J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (22) : 3189 - 3196
  • [6] Synthesis of a naphtho[2,3-c]pyranone as a model for the construction of the lactone ring
    Hugo, VI
    Oosthuizen, FJ
    Green, IR
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (09) : 1425 - 1432
  • [7] Microwave-assisted Claisen rearrangement on a silica gel support
    Kotha, S
    Mandal, K
    Deb, AC
    Banerjee, S
    [J]. TETRAHEDRON LETTERS, 2004, 45 (52) : 9603 - 9605
  • [8] A new protocol for benzoannulation by double Claisen rearrangement and ring-closing metathesis reactions as key steps
    Kotha, S
    Mandal, K
    [J]. TETRAHEDRON LETTERS, 2004, 45 (12) : 2585 - 2588
  • [9] MASQUELIN T, 1995, SYNTHESIS-STUTTGART, P780, DOI 10.1055/s-1995-3992
  • [10] Anionic Snieckus-Fries rearrangement: Solvent effects and role of mixed aggregates
    Riggs, Jason C.
    Singh, Kanwal J.
    Yun, Ma
    Collum, David B.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13709 - 13717
12