Efficient synthesis of dihydropyrido[4,3-d]pyrimidines by microwave-promoted three-component aza-Diels-Alder reaction

被引：18
作者：
Sarmah, Manas M. [1 ]
Sarma, Rupam [1 ,2 ]
Prajapati, Dipak [1 ]
Hu, Wenhao [3 ]
机构：
[1] CSIR NE Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India
[2] Nalbari Coll, Dept Chem, Nalbari 781335, Assam, India
[3] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 03期
关键词：
Aza-Diels-Alder reaction (ADA); Pyrido[4,3-d]pyrimidine; Multi-component reaction (MCR); Green chemistry; TYROSINE KINASE INHIBITORS; ONE-POT SYNTHESIS; KETONES; CYCLIZATION; PYRIMIDINE; CATALYST;
D O I：
10.1016/j.tetlet.2012.11.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A microwave-promoted solvent- and catalyst-free aza-Diels-Alder reaction is described. 6-[2-(dimethylamino)vinyl]-1,3-dimethyluracil reacts with aldehyde and amine inside a microwave reactor to produce dihydropyrido[4,3-d]pyrimidine derivatives in excellent yield and within a yew short time. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：267 / 271
页数：5
相关论文
共 45 条
  • [1] Synthesis and Characterization of Fused Pyrrolo[3,2-d:4,5-d′]bisthiazole-Containing Polymers
    Al-Hashimi, Mohammed
    Labram, John G.
    Watkins, Scott
    Motevalli, Majid
    Anthopoulos, Thomas D.
    Heeney, Martin
    [J]. ORGANIC LETTERS, 2010, 12 (23) : 5478 - 5481
  • [2] Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol
    Alaimo, Peter J.
    O'Brien, Robert
    Johnson, Adam W.
    Slauson, Sarah R.
    O'Brien, Jeannette M.
    Tyson, Elizabeth L.
    Marshall, Amanda-Lynn
    Ottinger, Colleen E.
    Chacon, Jon G.
    Wallace, Lorien
    Paulino, Corey Y.
    Connell, Sarah
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5111 - 5114
  • [3] [Anonymous], HETERO DIELS ALDER M
  • [4] Synthesis of δ-thiolactams by the aza-Diels-Alder reaction of in situ generated allenyltrimethylsilylthioketenes with imines
    Aoyagi, Shigenobu
    Hakoishi, Michiko
    Suzuki, Mariko
    Nakanoya, Yusuke
    Shimada, Kazuaki
    Takikawa, Yuji
    [J]. TETRAHEDRON LETTERS, 2006, 47 (44) : 7763 - 7766
  • [5] STRUCTURE ACTIVITY RELATIONSHIPS OF DIHYDROFOLATE-REDUCTASE INHIBITORS
    BLANEY, JM
    HANSCH, C
    SILIPO, C
    VITTORIA, A
    [J]. CHEMICAL REVIEWS, 1984, 84 (04) : 333 - 407
  • [6] Castle R. N., 1984, COMPREHENSIVE HETERO, P329, DOI DOI 10.1016/B978-008096519-2.00039-4
  • [7] Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines
    Cikotiene, Inga
    Kairys, Visvaldas
    Buksnaitiene, Rita
    Morkunas, Marius
    Rudys, Simonas
    Brukstus, Algirdas
    Fernandes, Miguel X.
    [J]. TETRAHEDRON, 2009, 65 (29-30) : 5752 - 5759
  • [8] An efficient aqueous microwave-assisted Suzuki-Miyaura cross-coupling reaction in the thiazole series
    Cohen, Anita
    Crozet, Maxime D.
    Rathelot, Pascal
    Vanelle, Patrice
    [J]. GREEN CHEMISTRY, 2009, 11 (11) : 1736 - 1742
  • [9] Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
  • [10] 2-B
12345