Synthesis of 3-Amino-8-azachromans and 3-Amino-7-azabenzofurans via Inverse Electron Demand Diels-Alder Reaction

被引:8
|
作者
Badarau, Eduard [1 ,2 ]
Suzenet, Franck [1 ]
Finaru, Adriana-Luminita [2 ]
Guillaumet, Gerald [1 ]
机构
[1] Univ Orleans, CNRS, UMR 6005, Inst Chim Organ & Analyt,UFR Sci, F-45067 Orleans 2, France
[2] Univ Bacau, Bacau 600115, Romania
关键词
Heterocycles; Cycloaddition; Polycycles; SEROTONIN; 5-HT7; RECEPTOR; FACILE SYNTHESIS; DERIVATIVES; 1,2,4-TRIAZINES; FURO<2,3-B>PYRIDINES; FUROPYRIDINES; ALDEHYDES; AGONISTS; INHIBITORS; CHROMAN;
D O I
10.1002/ejoc.200900191
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 3-amino-8-azachromans and 3-amino-7-azabenzofurans derivatives is reported. The synthetic strategy is based on an inverse electron demand Diels-Alder approach, which employs 1,2,4-triazines that are judiciously substituted with amino alkynols. This approach permits the variation of the substituent on the aromatic core and on the amine moiety, as well as of the size of the nonaromatic ring. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:3619 / 3627
页数:9
相关论文
共 50 条
  • [31] A novel double 'inverse electron-demand' Diels-Alder reaction of azolyldienamines and tetrazines
    Kotschy, A
    Novák, Z
    Vincze, Z
    Smith, DM
    Hajós, G
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6313 - 6316
  • [32] The inverse-electron demand Diels-Alder reaction of tetrazines with cyclic enol ethers
    Schafzahl, Bettina
    Knall, Astrid C.
    Slugovc, Christian
    MONATSHEFTE FUR CHEMIE, 2023, 154 (12): : 1383 - 1390
  • [33] Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones
    Li, Pingfan
    Yamamoto, Hisashi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [34] 7-SUBSTITUTED CYCLOHEPTATRIENES AS DIENOPHILES IN THE DIELS-ALDER CYCLOADDITION WITH INVERSE ELECTRON DEMAND
    BAUMANN, L
    KAMPCHEN, T
    SEITZ, G
    CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (01): : 171 - 176
  • [35] Total syntheses of ericifolione and its analogues via a biomimetic inverse-electron-demand Diels-Alder reaction
    Zhou, Tingting
    Zheng, Anquan
    Huo, Luqiong
    Li, Changgeng
    Tan, Haibo
    Wang, Sasa
    Chen, Huiyu
    CHEMICAL COMMUNICATIONS, 2021, 58 (02) : 270 - 273
  • [36] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 5-NITROPYRIMIDINE WITH ENAMINES - SYNTHESIS OF 3-NITROPYRIDINE DERIVATIVES
    MARCELIS, ATM
    VANDERPLAS, HC
    TETRAHEDRON, 1989, 45 (09) : 2693 - 2702
  • [37] Intramolecular hetero Diels-Alder with inverse electron demand: Synthesis of pyrano[3,2-b]indole derivatives
    Davion, Y
    Joseph, B
    Merour, JY
    SYNLETT, 1998, (10) : 1051 - +
  • [38] LEWIS ACID CATALYZED DIELS-ALDER REACTION WITH INVERSE ELECTRON DEMAND - ALTERNATIVE SYNTHESIS OF ALPHA-DAMASCONE
    COOKSON, RC
    TUDDENHAM, RM
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (19) : 742 - 742
  • [39] Synthesis of Constrained a-Amino Acid Derivatives via Diels-Alder Approach
    Kotha, S.
    Brahmachary, E.
    Sreenivasachary, N.
    Tetrahedron Letters, 39 (23):
  • [40] Reaction Rates of Various N-Acylenamines in the Inverse-Electron-Demand Diels-Alder Reaction
    Engelsma, Sander B.
    van den Ende, Thomas C.
    Overkleeft, Hermen S.
    van der Marel, Gijsbert A.
    Filippov, Dmitri V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2587 - 2591