The preparation of 2-substituted-3-diazoquinolin-4-ones

被引:2
|
作者
Simacek, Adam [1 ]
Hradilova, Ludmila [1 ,2 ]
Dvorakova, Barbora [1 ,2 ]
Jedinak, Lukas [1 ]
Bertolasi, Valerio [3 ]
Hradil, Pavel [1 ,2 ]
机构
[1] Palacky Univ, Dept Organ Chem, Olomouc 77146, Czech Republic
[2] Farmak As, Olomouc 77117, Czech Republic
[3] Univ Ferrara, Ctr Strutturist Diffrattometr, Dipartimento Sci Chim & Farmaceut, I-44100 Ferrara, Italy
关键词
Heterocycles; Quinolones; Diazo compound; Aminoquinoline; Substitutions;
D O I
10.1016/j.tetlet.2014.09.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2-substituted-3-diazoquinolin-4-ones is prepared by the reaction of 2-substituted-3-amino-4-chloroquinolines with sodium nitrite in sulfuric acid. Some of the obtained products are then utilised in triazole formation, reduction and a Wolff rearrangement/Friedel-Crafts ketene capture. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码:53 / 55
页数:3
相关论文
共 50 条
  • [1] A FACILE PREPARATION OF 3-SUBSTITUTED 2-THIOXO-TETRAHYDROQUINAZOLIN-4-ONES BY THE REACTION OF ANTHRANILAMIDE WITH ISOTHIOCYANATES
    CHAN, CH
    SHISH, FJ
    LIU, KC
    CHERN, JW
    HETEROCYCLES, 1987, 26 (12) : 3193 - 3196
  • [2] DIMETHYLHYDRAZONES OF SUBSTITUTED 4-PHENYL-3-BUTEN-2-ONES
    UNTERHALT, B
    ARCHIV DER PHARMAZIE, 1982, 315 (02) : 178 - 181
  • [3] A general approach for the synthesis of 5-substituted-4-amino-pyrrolidin-2-ones and 5-substituted-4-amino-3-pyrrolin-2-ones
    Pinheiro, Sergio
    da Silva Junior, Ronaldo C.
    de Souza, Acacio Silva
    de M. Carneiro, Jose Walkimar
    Muri, Estela M. F.
    Antunes, O. A. C.
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2402 - 2404
  • [4] Preparation of bicyclic guanidines by the iodocyclization of 3-alkenyl-2-(substituted amino)-1-imidazolin-4-ones
    Noguchi, M
    Okada, H
    Watanabe, M
    Moriyama, H
    Nakamura, O
    Kakehi, A
    HETEROCYCLIC COMMUNICATIONS, 1996, 2 (04) : 361 - 370
  • [5] PREPARATION OF SOME 3-CHLORO-SUBSTITUTED-2,6-DIARYLPIPERID IN 4-ONES
    PILLAY, MK
    MOHAMED, MIF
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1993, 70 (03) : 257 - 258
  • [6] A CONVENIENT PREPARATION OF SUBSTITUTED 2,5-DIBENZYLIDENECYCLOPENT-3-EN-1-ONES
    DESIRAJU, GR
    KISHAN, KVR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1988, 27 (10): : 953 - 954
  • [7] A SIMPLE STRATEGY FOR THE PREPARATION OF 6-SUBSTITUTED 3H-BENZOXAZOL-2-ONES AND 3H-BENZOTHIAZOL-2-ONES
    DeOrazio, Russell J.
    Maeng, Jun-Ho
    Manning, David D.
    Sherer, Brian A.
    Scott, Ian L.
    Nikam, Sham S.
    SYNTHETIC COMMUNICATIONS, 2011, 41 (23) : 3551 - 3555
  • [8] PREPARATION OF EXOCYCLIC AND ENDOCYCLIC AMINOXYL RADICALS OF 2-AMINO-SUBSTITUTED QUINAZOLIN-4(3H)-ONES
    OMELKA, L
    SVETLIK, J
    MAGNETIC RESONANCE IN CHEMISTRY, 1995, 33 (10) : 844 - 847
  • [9] Synthesis of 4-substituted-1,5-dihydro-2H-pyrrol-2-ones, potential synthons for the preparation of radiolabeled 3-substituted-γ-amino acids
    Vaccher, C
    SYNTHETIC COMMUNICATIONS, 2001, 31 (10) : 1481 - 1487
  • [10] Synthesis of 2-substituted 3-iodo-4H-chromen-4-ones
    Myannik, K. A.
    Yarovenko, V. N.
    Krayushkin, M. M.
    Levchenko, K. S.
    RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 543 - 545