α-Haloarylsulfonamides: multiple cyclization pathways to skeletally diverse benzofused sultams

被引:79
作者
Rayabarapu, Dinesh Kumar [1 ,2 ]
Zhou, Aihua [1 ,2 ]
Jeon, Kyu Ok [1 ,2 ]
Samarakoon, Thiwanka [1 ,2 ]
Rolfe, Alan [1 ,2 ]
Siddiqui, Hina [1 ,2 ]
Hanson, Paul R. [1 ,2 ]
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
[2] Univ Kansas, Ctr Chem Methodol & Lib Dev, Lawrence, KS 66047 USA
关键词
ORIENTED SYNTHESIS; DERIVATIVES; METATHESIS; MICHAEL; AGENTS;
D O I
10.1016/j.tet.2008.11.053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of new methods to skeletally diverse sultams based oil a central alpha-halo benzene sulfonamide building block is reported. Several salient features of this building block are Utilized ill multiple reaction pathways, including the Fleck reaction, C- and O-arylation, Sonogashira-Pauson-Khand, Sonogashira-intramolecular hydroamination, and domino aza-Michael-Heck for the generation of five-, six-, and seven-membered benzofused bicyclic and tricyclic sultams. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3180 / 3188
页数:9
相关论文
共 39 条
  • [21] Metal-initiated amination of alkenes and alkynes
    Muller, TE
    Beller, M
    [J]. CHEMICAL REVIEWS, 1998, 98 (02) : 675 - 703
  • [22] Diversity-oriented synthesis - Towards the optimal screening collection: A synthesis strategy
    Nielsen, Thomas E.
    Schreiber, Stuart L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 48 - 56
  • [23] Safe and convenient procedure for solvent purification
    Pangborn, AB
    Giardello, MA
    Grubbs, RH
    Rosen, RK
    Timmers, FJ
    [J]. ORGANOMETALLICS, 1996, 15 (05) : 1518 - 1520
  • [24] Direct comparison of the response of bicyclic sultam and lactam dienes to photoexcitation. Concerning the propensity of differing bond types to bridgehead nitrogen for homolytic cleavage
    Paquette, Leo A.
    Dura, Robert D.
    Fosnaugh, Nathan
    Stepanian, Marshall
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) : 8438 - 8445
  • [25] Rabasseda Xavier, 1994, Drugs of Today, V30, P557
  • [26] Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects
    Ritleng, V
    Sirlin, C
    Pfeffer, M
    [J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1731 - 1769
  • [27] Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1.1-Dioxido-1,2-benzisothiazoline-3-acetic Acid
    Rolfe, Alan
    Young, Kyle
    Hanson, Paul R.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) : 5254 - 5262
  • [28] Anticancer and antiviral sulfonamides
    Scozzafava, A
    Owa, T
    Mastrolorenzo, A
    Supuran, CT
    [J]. CURRENT MEDICINAL CHEMISTRY, 2003, 10 (11) : 925 - 953
  • [29] Pyrrolo[1,2-b][1,2,5] benzothiadiazepines (PBTDs):: A new class of agents with high apoptotic activity in chronic myelogenous leukemia K562 cells and in cells from patients at onset and who were imatinib-resistant
    Silvestri, Romano
    Marfe, Gabriella
    Artico, Marino
    La Regina, Giuseppe
    Lavecchia, Antonio
    Novellino, Ettore
    Morgante, Manuela
    Di Stefano, Carla
    Catalano, Gianfranco
    Filomeni, Giuseppe
    Abruzzese, Elisabetta
    Ciriolo, Maria Rosa
    Russo, Matteo Antonio
    Amadori, Sergio
    Cirilli, Roberto
    La Torre, Francesco
    Salimei, Paola Sinibaldi
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (19) : 5840 - 5844
  • [30] Diversity-oriented synthesis
    Spandl, Richard J.
    Diaz-Gavilan, Monica
    O'Connell, Kieron M. G.
    Thomas, Gemma L.
    Spring, David R.
    [J]. CHEMICAL RECORD, 2008, 8 (03) : 129 - 142