N-Tosylhydrazones: versatile synthons in the construction of cyclic compounds

被引:310
作者
Xia, Ying [1 ]
Wang, Jianbo [1 ]
机构
[1] Peking Univ, BNLMS, Coll Chem, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, Beijing 100871, Peoples R China
关键词
GENERATED IN-SITU; PALLADIUM-CATALYZED INSERTION; TANDEM CYCLOADDITION REACTIONS; CARBENE MIGRATORY INSERTION; METAL-FREE CYCLOPROPANATION; CROSS-COUPLING REACTIONS; BOND FORMATION SYNTHESIS; AZIDE-FREE CONDITIONS; C-C BOND; DIAZO-COMPOUNDS;
D O I
10.1039/c6cs00737f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Tosylhydrazones have recently emerged as useful synthons in a variety of transition-metal-catalyzed and transition-metal-free reactions, which affords novel methodologies for the formation of carboncarbon and carbon-heteroatom bonds. In this context, it has been found that N-tosylhydrazones can be used as versatile building blocks in the construction of a range of cyclic compounds. In this review, cyclization reactions based on N-tosylhydrazones as substrates are discussed. A series of cyclic compounds, including aromatic and non-aromatic ring systems, are demonstrated to be easily constructed by cyclizations with N-tosylhydrazones.
引用
收藏
页码:2306 / 2362
页数:57
相关论文
共 178 条
  • [1] Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ
    Adams, LA
    Aggarwal, VK
    Bonnert, RV
    Bressel, B
    Cox, RJ
    Shepherd, J
    de Vicente, J
    Walter, M
    Whittingham, WG
    Winn, CL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9433 - 9440
  • [2] Simple preparation of trans-epoxides via ylide intermediates
    Aggarwal, VK
    Aragoncillo, C
    Winn, CL
    [J]. SYNTHESIS-STUTTGART, 2005, (08): : 1378 - 1382
  • [3] Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones.: Synthesis of a mevinic acid analogue and (+)-prelactone B
    Aggarwal, VK
    Bae, I
    Lee, HY
    [J]. TETRAHEDRON, 2004, 60 (43) : 9725 - 9733
  • [4] A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ
    Aggarwal, VK
    de Vicente, J
    Bonnert, RV
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) : 5381 - 5383
  • [5] A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities
    Aggarwal, VK
    Alonso, E
    Bae, I
    Hynd, G
    Lydon, KM
    Palmer, MJ
    Patel, M
    Porcelloni, M
    Richardson, J
    Stenson, RA
    Studley, JR
    Vasse, JL
    Winn, CL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10926 - 10940
  • [6] Synthesis of epoxides from aldehydes and tosylhydrazone salts catalysed by triphenylarsine:: complete trans selectivity for all combinations of coupling partners
    Aggarwal, VK
    Patel, M
    Studley, J
    [J]. CHEMICAL COMMUNICATIONS, 2002, (14) : 1514 - 1515
  • [7] Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines
    Aggarwal, VK
    de Vicente, J
    Bonnert, RV
    [J]. ORGANIC LETTERS, 2001, 3 (17) : 2785 - 2788
  • [8] Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO
  • [9] 2-W
  • [10] Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1433, DOI 10.1002/1521-3773(20010417)40:8<1433::AID-ANIE1433>3.0.CO