The Ritter reaction of N-(hydroxymethyl)saccharin with nitriles

被引：0
|
作者：
de Oliveira, Marllon Nascimento [1 ]
de Mattos, Marcio C. S. [1 ,2 ]
机构：
[1] Univ Fed Rio De Janeiro, Dept Quim Organ, Inst Quim, Rio De Janeiro, Brazil
[2] Univ Fed Rio De Janeiro, Dept Quim Organ, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2024年 / 61卷 / 01期
关键词：
SACCHARIN DERIVATIVES; BIOLOGICAL EVALUATION; COHALOGENATION; INHIBITORS; DESIGN;
D O I：
10.1002/jhet.4743
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of the Ritter reaction ofN-(hydroxymethyl)saccharin withnitriles for the synthesis ofN-[(saccharinyl)methyl]amides is reported. Thesuccess of this reaction relies on an operationally simple procedure and on theuse of inexpensive reagents. The present method enables access to a variety ofsaccharin scaffolds of potential interest in medicinal chemistry in moderate tohigh yields. Furthermore, the scalability of this reaction was demonstrated bya multigram-scale transformation, without any loss of efficiency.
引用
收藏
页码：188 / 193
页数：6
相关论文
共 50 条
  • [1] THE REACTION OF N-HYDROXYMETHYL PHTHALIMIDE WITH NITRILES
    BUC, SR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (02) : 254 - 256
  • [2] REACTION OF N-(PHENYLSULFONYL)SACCHARIN WITH AMINES
    IMAI, Y
    OKUNOYAMA, H
    HIRATA, K
    UEDA, M
    [J]. NIPPON KAGAKU KAISHI, 1982, (01) : 111 - 114
  • [3] AMIDES FROM NITRILES + ALCOHOLS BY RITTER REACTION
    SANGUIGNI, JA
    LEVINE, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (04) : 573 - &
  • [4] SYNTHESES WITH NITRILES .28. CONTRIBUTIONS TO RITTER REACTION
    JUNEK, H
    STOLZ, G
    [J]. MONATSHEFTE FUR CHEMIE, 1970, 101 (04): : 1234 - &
  • [5] An Efficient Way to Synthesize N-(β-nitroalkyl) Amides Through Ritter Reaction
    Shi, Ronghua
    Ai, Wensi
    He, Tao
    Ma, Xiaobo
    Qian, Shan
    Wang, Zhouyu
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2015, 12 (10) : 720 - 726
  • [6] N-(Hydroxymethyl)ibogaine
    Jarraya, Raoudha Mezghani
    Bouaziz, Amira
    Hamdi, Besma
    Ben Salah, Abdelhamid
    Damak, Mohamed
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1739 - U1774
  • [7] N-(hydroxymethyl) melamines
    Coley, HM
    [J]. GENERAL PHARMACOLOGY, 1997, 28 (02): : 177 - 182
  • [8] Organocatalytic synthesis of amides from nitriles via the Ritter reaction
    Khaksar, Samad
    Fattahi, Eskandar
    Fattahi, Esmail
    [J]. TETRAHEDRON LETTERS, 2011, 52 (45) : 5943 - 5946
  • [9] Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts
    A. R. Bayguzina
    A. R. Lutfullina
    R. I. Khusnutdinov
    [J]. Russian Journal of Organic Chemistry, 2018, 54 : 1127 - 1133
  • [10] Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts
    Bayguzina, A. R.
    Lutfullina, A. R.
    Khusnutdinov, R. I.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (08) : 1127 - 1133
12345