Stereoselective synthesis of a 2,3-disubstituted 5-pyrrolidinone derivative of quinazolin-4(3H)-one

被引:0
|
作者
Szabo, M
Kokosi, J
Kovacs, A
Bocskei, Z
Hermecz, I
机构
[1] Semmelweis Univ Med, Inst Pharmaceut Chem, H-1092 Budapest, Hungary
[2] Tech Univ, Dept Gen & Analyt Chem, H-1114 Budapest, Hungary
[3] Chinoin Chem & Pharmaceut Works Ltd, H-1325 Budapest, Hungary
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermal cyclization of acetoacetamide (3), prepared from 2-[1'-(p-methoxyphenylaminoethyl]quinazolin-4(3H)-one (2) and ethyl acetoacetate, resulted in the formation of 2-(5-oxopyrrolidin-2-yl)quinazolin-4(3H)-one (6) with high selectivity in excellent yield. The stereostructure of 6 was investigated by NMR spectroscopy, and determined by X-Ray investigations.
引用
收藏
页码:2437 / 2442
页数:6
相关论文
共 50 条
  • [21] Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
    Peng, Jin-Bao
    Geng, Hui-Qing
    Wang, Wei
    Qi, Xinxin
    Ying, Jun
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2018, 365 : 10 - 13
  • [22] Synthesis and antitumor activity of some 2, 3-disubstituted quinazolin-4(3H)-ones and 4, 6-disubstituted-1, 2, 3, 4-tetrahydroquinazolin-2H-ones
    Gawad, Nagwa M. Abdel
    Georgey, Hanan H.
    Youssef, Riham M.
    El-Sayed, Nehad A.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 6058 - 6067
  • [23] Synthesis and Cytotoxicity of Quinazolin-4(3H)-one Based Peptides
    Shankaraiah, P.
    Bhavani, A. K. D.
    Kumar, A. Kishore
    Ramakrishna, K.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2020, 90 (04) : 720 - 724
  • [24] Synthesis and Cytotoxicity of Quinazolin-4(3H)-one Based Peptides
    P. Shankaraiah
    A. K. D. Bhavani
    A. Kishore Kumar
    K. Ramakrishna
    Russian Journal of General Chemistry, 2020, 90 : 720 - 724
  • [25] An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy
    Murthy, V. Narayana
    Nikumbh, Satish P.
    Kumar, S. Praveen
    Rao, L. Vaikunta
    Raghunadh, Akula
    TETRAHEDRON LETTERS, 2015, 56 (42) : 5767 - 5770
  • [26] ONE-POT SYNTHESIS OF 2,3-DISUBSTITUTED QUINAZOLIN-4-ONES
    ASHARE, R
    MUKERJEE, AK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (11): : 1180 - 1181
  • [27] A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives
    Zhichkin, Paul
    Kesicki, Edward
    Treiberg, Jennifer
    Bourdon, Lisa
    Ronsheim, Matthew
    Ooi, Hua Chee
    White, Stephen
    Judkins, Angela
    Fairfax, David
    ORGANIC LETTERS, 2007, 9 (07) : 1415 - 1418
  • [28] SYNTHESIS OF ISOXAZOLYL QUINAZOLIN-4 (3H)-ONES
    Rajanarendar, E.
    Venkateshwarlu, P.
    Ramakrishna, S.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 22 (02) : 95 - 98
  • [29] Synthesis of quinazolin-4(3H)-ones, an update
    Picos-Corrales, Lorenzo A.
    Sarmiento-Sanchez, Juan I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (08) : 762 - 764
  • [30] Ecofriendly synthesis of quinazolin-4(3H)-ones
    Kidwai, M
    Rastogi, R
    Rastogi, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (02): : 423 - 425