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] A Study on Sulfonylation of Cyanohydrins with α-Functionalized Sulfonyl Chlorides
    Dobrydnev, Alexey, V
    Vashchenko, Bohdan V.
    Popova, Maria, V
    Volovenko, Yulian M.
    CHEMISTRYSELECT, 2022, 7 (30):
  • [2] Regioselective Chlorothiolation of Alkenes with Sulfonyl Chlorides
    Wei, Jingjing
    Liang, Shuaishuai
    Jiang, Lvqi
    Mumtaz, Yasir
    Yi, Wen-bin
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) : 977 - 984
  • [3] Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides
    Bogolubsky, Andrey V.
    Moroz, Yurii S.
    Mykhailiuk, Pavel K.
    Pipko, Sergey E.
    Konovets, Anzhelika I.
    Sadkova, Irina V.
    Tolmachev, Andrey
    ACS COMBINATORIAL SCIENCE, 2014, 16 (04) : 192 - 197
  • [4] Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides
    Ilkin, Vladimir
    Berseneva, Vera
    Beryozkina, Tetyana
    Glukhareva, Tatiana
    Dianova, Lidia
    Dehaen, Wim
    Seliverstova, Eugenia
    Bakulev, Vasiliy
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2937 - 2947
  • [5] Base-Free Method for Preparation of O-Sulfonyl Aldoximes Starting from Aldoximes and Sulfonyl Chlorides
    Deng, Guisheng
    Mo, Honghua
    Luo, Jing
    Tang, Li
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (11) : 2177 - 2180
  • [6] Synthesis of isomeric fluoronitrobenzene-sulfonyl chlorides
    Zhersh, Sergey
    Lukin, Oleg
    Matvienko, Vitaly
    Tolmachev, Andrey
    TETRAHEDRON, 2010, 66 (32) : 5982 - 5986
  • [7] TBAI-mediated regioselective sulfenylation of indoles with sulfonyl chlorides in one pot
    He, Yongzhao
    Jiang, Jun
    Bao, Wenhu
    Deng, Wei
    Xiang, Jiannan
    TETRAHEDRON LETTERS, 2017, 58 (49) : 4583 - 4586
  • [8] Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine
    Amabili, Paolo
    Amici, Adolfo
    Civitavecchia, Annafelicia
    Maggiore, Beatrice
    Orena, Mario
    Rinaldi, Samuele
    Tolomelli, Alessandra
    AMINO ACIDS, 2016, 48 (02) : 461 - 478
  • [9] Facile Synthesis of Sulfonyl Chlorides/Bromides from Sulfonyl Hydrazides
    Chen, Rongxiang
    Xu, Shaohong
    Shen, Fumin
    Xu, Canran
    Wang, Kaikai
    Wang, Zhanyong
    Liu, Lantao
    MOLECULES, 2021, 26 (18):
  • [10] Synthesis and biological evaluation of structurally diverse α-conformationally restricted chalcones and related analogues
    Maguire, Casey J.
    Carlson, Graham J.
    Ford, Jacob W.
    Strecker, Tracy E.
    Hamel, Ernest
    Trawick, Mary Lynn
    Pinney, Kevin G.
    MEDCHEMCOMM, 2019, 10 (08) : 1445 - 1456