Synthesis and transformations of pyrrolo[1,2-a][1,3,5]-triazines

被引：4
|
作者：
Verhoeven, Jonas [1 ,2 ]
Reddy, B. Narendraprasad [1 ,2 ]
Meerpoel, Lieven [3 ]
Thuring, Jan Willem [3 ]
Verniest, Guido [1 ,2 ,3 ]
机构：
[1] Vrije Univ Brussel, Fac Sci & Bioengn Sci, Dept Chem, Res Grp Organ Chem, Pl Laan 2, B-1050 Brussels, Belgium
[2] Vrije Univ Brussel, Fac Sci & Bioengn Sci, Dept Bioengn Sci, Pl Laan 2, B-1050 Brussels, Belgium
[3] Janssen Res & Dev, Turnhoutseweg 30, B-2340 Beerse, Belgium
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 52期
关键词：
Pyrrolotriazines; Bromination; Cyclocondensation; Aminopyrrole; Nucleoside analogues; REDUCTION; ANALOGS;
D O I：
10.1016/j.tetlet.2018.11.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pyrrolotriazines and related fused azaheterocycles have high potential for the synthesis of bioactive compounds, especially as a purine base isoster in carbon linked nucleosides. Although many structurally related compounds have already been synthesized and used in medicinal chemistry, pyrrolo[1,3,5]triazines have barely been described. The present work describes the synthesis of such heterocycles via condensation of 2-amino-3-ethoxycarbonylpyrrole with ethoxycarbonyliso(thio)cyanate. In a brief reactivity study of the obtained fused pyrroles, O- and S-alkylation, ester hydrolysis as well as regioselective bromination at the 6-position was demonstrated. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4537 / 4539
页数：3
相关论文
共 50 条
  • [1] Regioselective synthesis of imidazo[1,2-a][1,3,5]triazines and 3,4-dihydroimidazo[1,2-a][1,3,5]triazines from [1,3,5]triazin-2,4-diamines
    Dao, Pascal
    Garbay, Christiane
    Chen, Huixiong
    TETRAHEDRON, 2013, 69 (19) : 3867 - 3871
  • [2] Diastereoselective synthesis of pyrimido[1,2-a][1,3,5]triazines based on the Biginelli reaction
    Van Quy, Do
    Kruzhilin, Alexey A.
    Stolpovskaya, Nadezhda, V
    Baranin, Sergey, V
    Prezent, Mikhail A.
    Minyaev, Mikhail E.
    Shikhaliev, Khidmet S.
    TETRAHEDRON, 2023, 134
  • [3] SYNTHETIC ROUTES TOWARDS PYRIMIDO[1,2-a][1,3,5]TRIAZINES (REVIEW)
    Dolzhenko, Anton V.
    HETEROCYCLES, 2011, 83 (07) : 1489 - 1525
  • [4] A FACILE SYNTHESIS OF PYRROLO[1,2-A]PYRIMIDINES AND PYRROLO[1,2-A]IMIDAZOLES
    ROSS, JR
    VISHWAKARMA, LC
    SOWELL, JW
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 661 - 665
  • [5] SYNTHESIS OF NEW 1-ARYL-6-BENZYLIMIDAZO[1,2-a][1,3,5]TRIAZINES WITH POTENTIAL PHARMACOLOGICAL ACTIVITY
    Rzadkowska, Marzena
    Szacon, Elzbieta
    Matosiuk, Dariusz
    Kedzierska, Ewa
    Fidecka, Sylwia
    ACTA POLONIAE PHARMACEUTICA, 2012, 69 (06): : 1270 - 1275
  • [6] A facile synthesis of pyrrolo [1,2-a] imidazoles and pyrrolo-[1,2-a] pyrimidines
    Singh, OM
    Ahmed, MF
    Dinesh, H
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 15 (01) : 87 - 88
  • [7] Synthesis of imidazo[1,2-a][1,3,5]triazines by NBS-mediated coupling of 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds
    Pan, Zexi
    Song, Chan
    Zhou, Wei
    Cui, Dong-Mei
    Zhang, Chen
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (16) : 6182 - 6185
  • [8] Diversity-oriented synthesis of imidazo[1,2-a][1,3,5]triazine derivatives from 2-amine-[1,3,5]triazines with ketones
    Zhao, Wanqiu
    Zhang, Cheng
    Zhong, Pengzhen
    Zhou, Wei
    Zhang, Chen
    Cui, Dong-Mei
    CHEMICAL COMMUNICATIONS, 2021, 57 (82) : 10715 - 10718
  • [9] SYNTHESIS OF PYRROLO[1,2-A]QUINOLINES
    BOUYAZZA, L
    LANCELOT, JC
    RAULT, S
    ROBBA, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (01) : 77 - 80
  • [10] Synthesis of novel pyrido[1,2-a][1,3,5]triazine derivatives
    Dotsenko, V. V.
    Krivokolysko, S. G.
    Litvinov, V. P.
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (04): : 621 - 622
12345