Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation

被引：16
|
作者：
Ramanathan, Mani [1 ]
Hsu, Ming-Tsung [1 ]
Liu, Shiuh-Tzung [1 ]
机构：
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
来源：
TETRAHEDRON | 2019年 / 75卷 / 06期
关键词：
Quinazolinone; Diazonium; Nitrilium; Nitrile; Annulation; CHEMISTRY; QUINAZOLINONES; AFLOQUALONE; INHIBITORS; POTENT;
D O I：
10.1016/j.tet.2018.12.065
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：791 / 796
页数：6
相关论文
共 50 条
  • [31] Mass spectrometer as a probe in the synthesis of 2-substituted-4(3H)-quinazolinones
    Ramana, DV
    Sundaram, N
    Yuvaraj, TE
    Babu, BG
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (08): : 905 - 908
  • [32] POTENTIAL CNS ACTIVE AGENTS .2. STUDIES OF 4(3H)-QUINAZOLINONES
    LAKHAN, R
    SINGH, RL
    FARMACO-EDIZIONE SCIENTIFICA, 1988, 43 (09): : 745 - 751
  • [33] REACTIONS OF 2,3-DISUBSTITUTED 4(3H)-QUINAZOLINONES AND RELATED COMPOUNDS
    BADR, MZA
    ELNAGGAR, GM
    ELSHERIEF, HAH
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1980, 19 (10): : 925 - 926
  • [34] SOME REACTIONS OF 2-HETEROCYCLE-4(3H)-QUINAZOLINONES WITH ELECTROPHILIC REAGENTS
    MURAOKA, K
    ICHIKAWA, M
    HISANO, T
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1980, 100 (04): : 375 - 385
  • [35] The synthesis of 2-amino-4(3H)-quinazolinones and related heterocycles via a mild electrocyclization of aryl guanidines
    Sales, Zachary S.
    Mani, Neelakandha S.
    Allison, Brett D.
    TETRAHEDRON LETTERS, 2018, 59 (17) : 1623 - 1626
  • [36] STUDIES IN QUINAZOLINES .3. SYNTHESIS OF 2-ALKYL-3-ARALKYL-4-(3H) AND 2-MERCAPTO-3-ARALKYL/ALKYL/-4(3H)-QUINAZOLINONES
    SATPANTHI, PS
    TRIVEDI, JP
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1971, 48 (11) : 1021 - +
  • [37] Concise synthesis of 2-amino-4(3H)-quinazolinones from simple (Hetero)aromatic amines
    Zeghida, Walid
    Debray, Julien
    Chierici, Sabine
    Durny, Pascal
    Demeunynck, Martine
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06): : 2473 - 2475
  • [38] PREPARATION AND BIOLOGICAL-ACTIVITY OF SOME 2-SUBSTITUTED 3-(4'CARBOXYPHENYL)-7-NITRO-4 (3H)-QUINAZOLINONES
    VARMA, RS
    BAHADUR, S
    AGNIHOTRI, AK
    POLISH JOURNAL OF PHARMACOLOGY AND PHARMACY, 1980, 32 (05): : 801 - 806
  • [39] UNUSUAL PRODUCTS IN MANNICH REACTION WITH 2-METHYL-3-SUBSTITUTED-4-(3H)-QUINAZOLINONES
    KIRMANI, MZ
    AHMED, SR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (08): : 748 - 750
  • [40] Mass spectrometer as a probe in the synthesis of 2-substituted-3-phenyl-4 (3H)-quinazolinones
    Ramana, DV
    Yuvaraj, TE
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 9 (03) : 173 - 180
12345