Streamlined access to 2,3-dihydropyrazino[1,2-a]indole-1,4-diones via Ugi reaction followed by microwave-assisted cyclization

被引：14
作者：
Tsirulnikov, Sergey [1 ]
Nikulnikov, Mikhail [1 ]
Kysil, Volodymyr [2 ]
Ivachtchenko, Alexandre [2 ]
Krasavin, Mikhail [1 ]
机构：
[1] Chem Divers Res Inst, Chimki 141400, Moscow Reg, Russia
[2] ChemDiv Inc, San Diego, CA 92121 USA
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 39期
关键词：
Isocyanide-based multi-component reactions; Post-Ugi modifications; Microwave-assisted synthesis; Combinatorial chemistry; DIELS-ALDER REACTION; DERIVATIVES; HETEROCYCLES; STRATEGY;
D O I：
10.1016/j.tetlet.2009.07.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method is developed to construct drug-like 2,3-dihydropyrazino[1,2-a]indole-1,4-diones from 1H-indole-2-carboxylic acids, ethyl pyruvate, isocyanides, and primary at-nines via a one-pot, two-step procedure involving Ugi reaction and microwave-assisted cyclization. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5529 / 5531
页数：3
相关论文
共 21 条
  • [1] Recent advances in the development and applications of post-Ugi transformations
    Akritopoulou-Zanze, Irini
    Djuric, Stevan W.
    [J]. HETEROCYCLES, 2007, 73 (01) : 125 - +
  • [2] Synthesis of substituted 3,4-dihydroquinolin-2(1H)-one derivatives by sequential Ugi/acrylanilide [6π]-photocyclizations
    Akritopoulou-Zanze, Irini
    Whitehead, Alan
    Waters, Jan E.
    Henry, Rodger F.
    Djuric, Stevan W.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (20) : 3549 - 3552
  • [3] Synthesis of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by sequential Ugi/[2+2] ene-enone photocycloadditions
    Akritopoulou-Zanze, Irini
    Whitehead, Alan
    Waters, Jan E.
    Henry, Rodger F.
    Djuric, Stevan W.
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1299 - 1302
  • [4] Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands
    Attia, Mohamed I.
    Witt-Enderby, Paula A.
    Julius, Justin
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (16) : 7654 - 7661
  • [5] Multicomponent synthesis of dihydrobenzoxazepinones by coupling Ugi and Mitsunobu reactions
    Banfi, Luca
    Basso, Andrea
    Guanti, Giuseppe
    Lecinska, Paulina
    Riva, Renata
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) : 4236 - 4240
  • [6] A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics
    Basso, Andrea
    Banfi, Luca
    Guanti, Giuseppe
    Riva, Renata
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (02) : 253 - 258
  • [7] A new class of highly cytotoxic diketopiperazines
    Boger, DL
    Fink, BE
    Hedrick, MP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (10) : 1019 - 1020
  • [8] Ugi-Post Functionalization, from a Single Set of Ugi-Adducts to Two Distinct Heterocycles by Microwave-Assisted Palladium-Catalyzed Cyclizations: Tuning the Reaction Pathways by Ligand Switch
    Erb, William
    Neuville, Luc
    Zhu, Jieping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) : 3109 - 3115
  • [9] Structure-based exploration of cyclic dipeptide chitinase inhibitors
    Houston, DR
    Synstad, B
    Eijsink, VGH
    Stark, MJR
    Eggleston, IM
    van Aalten, DMF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (23) : 5713 - 5720
  • [10] Novel applications of ethyl glyoxalate with the Ugi MCR
    Hulme, C
    Cherrier, MP
    [J]. TETRAHEDRON LETTERS, 1999, 40 (29) : 5295 - 5299
123