Gas-Phase Synthesis of Pyrazolo[3,4-b]pyridin-4-ones

被引：7
|
作者：
Mackay, Martha [1 ]
Nortcliffe, Andrew [1 ]
McNab, Hamish [1 ]
Hulme, Alison N. [1 ]
机构：
[1] Univ Edinburgh, EastCHEM Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 02期
关键词：
gas-phase reactions; pericyclic reactions; heterocycles; Meldrum's acid; medicinal chemistry; BIOLOGICAL EVALUATION; INHIBITORS; POTENT; PYROLYSIS; ACID;
D O I：
10.1055/s-0034-1378666
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Flash vacuum pyrolysis (FVP) at 500-600 degrees C of 1-substituted pyrazolylaminomethylene derivatives of Meldrum's acid provides 1-substituted pyrazolo[3,4-b]pyridin-4-ones in high yields. If the 1-substituent is a tert-butyl group, FVP at 750-850 degrees C causes elimination of 2-methyl-1-propene to give the parent pyrazolo[3,4-b]pyridin-4-one.
引用
收藏
页码：242 / 248
页数：7
相关论文
共 50 条
  • [21] Synthesis of 3-aminopyrazolo[3,4-b]pyridine-4-carbonitriles
    Maksimova, V. N.
    Naidenova, A. I.
    Ershov, O. V.
    Nasakin, O. E.
    Tafeenko, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (12) : 1830 - 1834
  • [22] Efficient synthesis of tetrahydro-1H-pyrazolo[3,4-b]pyridines based on the recyclization of N-arylitaconimides with aminopyrazoles
    Shmoylova, Yana Yu.
    Kovygin, Yuri A.
    Kosheleva, Evgeniya A.
    Shikhaliev, Khidmet S.
    Ledenyova, Irina V.
    Prezent, Mikhail A.
    MENDELEEV COMMUNICATIONS, 2022, 32 (05) : 688 - 690
  • [23] A simple synthesis of 1De-pyrazolo[3,4-b]pyridines
    Sizova, Ekaterina E.
    Arshinov, Evgenii V.
    Kotsareva, Yana A.
    Glizdinskaya, Larisa V.
    Sagitullina, Galina P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (09) : 1026 - 1032
  • [24] An efficient regioselective sonochemical synthesis of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones
    Abbas Azimi Roshan
    Manouchehr Mamaghani
    Nosrat Ollah Mahmoodi
    Farhad Shirini
    Chinese Chemical Letters, 2012, 23 (04) : 399 - 402
  • [25] Meglumine catalyzed one-pot green synthesis of novel 4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6-amines
    Govindaraju, Santhosh
    Tabassum, Sumaiya
    Khan, Riyaz-ur-Rahaman
    Pasha, Mohamed Afzal
    CHINESE CHEMICAL LETTERS, 2017, 28 (02) : 437 - 441
  • [26] Microwave-assisted palladium mediated efficient synthesis of pyrazolo[3,4-b]pyridines, pyrazolo[3,4-b]quinolines, pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a]quinazolines
    Shekarrao, Kommuri
    Kaishap, Partha Pratim
    Saddanapu, Venkateshwarlu
    Addlagatta, Anthony
    Gogoi, Sanjib
    Boruah, Romesh C.
    RSC ADVANCES, 2014, 4 (46) : 24001 - 24006
  • [27] SO3H-functionalized MCM-41 as an efficient catalyst for the combinatorial synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines
    Safaei, Shirin
    Mohammadpoor-Baltork, Iraj
    Khosropour, Ahmad Reza
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (07) : 1583 - 1589
  • [28] One-pot and step-wise synthesis of thieno[3,2-c] pyridin-4-ones
    Sahu, Satya Narayan
    Singh, Surjeet
    Shaw, Ranjay
    Shally
    Ram, Vishnu Ji
    Pratap, Ramendra
    RSC ADVANCES, 2016, 6 (88): : 85515 - 85520
  • [29] Deazapurine Analogues Bearing a 1H-Pyrazolo[3,4-b]pyridin-3(2H)-one Core: Synthesis and Biological Activity
    Supe, Linda
    Afzal, Saira
    Mahmood, Abid
    Ejaz, Syeda Abida
    Hein, Martin
    Iaroshenko, Viktor O.
    Villinger, Alexander
    Lecka, Joanna
    Sevigny, Jean
    Iqbal, Jamshed
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2629 - 2644
  • [30] Harnessing Cascade Suzuki-Cyclization Reactions of Pyrazolo[3,4-b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics
    Lavrard, Hubert
    Popowycz, Florence
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 600 - 608
12345