A Library of Conformationally Restricted Saturated Heterocyclic Sulfonyl Chlorides

被引：10
|
作者：
Zhersh, Sergey [1 ,2 ]
Buryanov, Volodymyr V. [1 ,2 ]
Karpenko, Oleksandr V. [1 ]
Grygorenko, Oleksandr O. [1 ,2 ]
Tolmachev, Andrey A. [1 ,2 ]
机构：
[1] Enamine Ltd, UA-01103 Kiev, Ukraine
[2] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine
来源：
SYNTHESIS-STUTTGART | 2011年 / 22期
关键词：
sulfonyl chlorides; nitrogen heterocycles; molecular rigidity; libraries; conformational restriction; INHIBITORS; ACID; DESIGN; PEPTIDOSULFONAMIDES; PEPTIDOMIMETICS; SULFINAMIDE; DERIVATIVES; DIVERSITY; PEPTIDES; REAGENTS;
D O I：
10.1055/s-0030-1260223
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An approach to the synthesis of conformationally restricted saturated heterocyclic sulfonyl chlorides is described. Being guided by the principle of diversity-oriented conformational restriction, a mini-library of saturated heterocyclic sulfonyl chlorides was designed and synthesized. The library consists of nine members that are derivatives of azetidine, pyrrolidine, and piperidine. These compounds were prepared in 19-88% total yields on multigram scale starting from the corresponding Cbz-protected amino alcohols.
引用
收藏
页码：3669 / 3674
页数：6
相关论文
共 50 条
  • [1] SOME HETEROCYCLIC SULFONYL CHLORIDES AND DERIVATIVES
    CREMLYN, RJ
    SWINBOURNE, FJ
    YUNG, KM
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (05) : 997 - 1006
  • [2] DIPOLE-MOMENTS AND CONFORMATIONS OF HETEROCYCLIC SULFONYL CHLORIDES
    GRUTTADAURIA, S
    MACCARONE, E
    PAPPALARDO, GC
    TOMASELLI, GA
    GAZZETTA CHIMICA ITALIANA, 1976, 106 (7-8): : 657 - 662
  • [3] A NOVEL CLASS OF CONFORMATIONALLY RESTRICTED HETEROCYCLIC MUSCARINIC AGONISTS
    SAUERBERG, P
    LARSEN, JJ
    FALCH, E
    KROGSGAARDLARSEN, P
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) : 1004 - 1009
  • [4] Heterocyclic pentafluorophenyl sulfonate esters as shelf stable alternatives to sulfonyl chlorides
    Bornholdt, Jan
    Fjaere, Karianne Wilhemsen
    Felding, Jakob
    Kristensen, Jesper Langgaard
    TETRAHEDRON, 2009, 65 (45) : 9280 - 9284
  • [5] CONFORMATIONALLY RESTRICTED RETINOIDS
    DAWSON, MI
    HOBBS, PD
    DERDZINSKI, K
    CHAN, RLS
    GRUBER, J
    CHAO, WR
    SMITH, S
    THIES, RW
    SCHIFF, LJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (11) : 1516 - 1531
  • [6] SULFINYL AND SULFONYL CHLORIDES BY CHLORINATION
    DOUGLASS, IB
    THOMAS, EG
    FARAH, BS
    JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06): : 1996 - &
  • [7] DESULFONATION OF ALKANESULFONATES AND SULFONYL CHLORIDES
    CARLSEN, PHJ
    RIST, O
    LUND, T
    HELLAND, I
    ACTA CHEMICA SCANDINAVICA, 1995, 49 (09): : 701 - 702
  • [8] OXIDATION OF PAPAIN BY SULFONYL CHLORIDES
    HARTMAN, SC
    FEDERATION PROCEEDINGS, 1969, 28 (02) : 858 - &
  • [9] FACILE SYNTHESIS OF SULFONYL CHLORIDES
    HUANG, JX
    WIDLANSKI, TS
    TETRAHEDRON LETTERS, 1992, 33 (19) : 2657 - 2660
  • [10] A NEW SYNTHESIS OF SULFONYL CHLORIDES
    KHARASCH, MS
    ZAVIST, AF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (10) : 3526 - 3526
12345