Amine-Promoted One-Pot, Multicomponent Route to Spiro-Fused-Pyran Derivatives in Aqueous Media

被引:4
|
作者
Alizadeh, Abdolali [1 ]
Rezvanian, Atieh [1 ]
Bayat, Fahimeh [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
关键词
Pyrans; spiro-fused; Ninhydrin; Malononitrile; 1,3-Diketones, cyclic; SINGLE POT;
D O I
10.1002/hlca.201300387
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The primary amine-promoted synthesis of spiro-fused-pyran derivatives via the three-component reaction of ninhydrin, malononitrile, and cyclic 1,3-diketo compounds is described. This new methodology affords the title compounds in high yields and short time, and with easy workup without chromatographic purification steps or extraction. All structures were confirmed by IR, H-1- and C-13-NMR spectroscopy, and mass spectroscopy. A plausible mechanism for this type of reaction is proposed (Scheme 2).
引用
收藏
页码:532 / 536
页数:5
相关论文
共 50 条
  • [21] Synthesis of pyrano[3,2-c]pyran-5-one derivatives by three-component one-pot reaction in aqueous media
    Shi, Da-Qing
    Niu, Li-Hui
    Zhuang, Qi-Ya
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (09) : 1633 - 1636
  • [22] Nano-ZnO Catalyzed Multicomponent One-Pot Synthesis of Novel Spiro(indoline-pyranodioxine) Derivatives
    Sachdeva, Harshita
    Saroj, Rekha
    Dwivedi, Diksha
    SCIENTIFIC WORLD JOURNAL, 2014,
  • [23] Facile One-Pot Synthesis of Functionalized Quinoline-Fused Fluorescent Dihydro/Spiro-quinazolinone Derivatives
    George, Kevin
    Elavarasan, Pavithra
    Ponnusamy, Shanmugam
    Sathananthan, Kannadasan
    ACS OMEGA, 2022, 7 (24): : 20605 - 20618
  • [24] One-pot Synthesis of 1,8-Dioxo-decahydroacridine Derivatives in Aqueous Media
    Balalaie, Saeed
    Chadegani, Fatemeh
    Darviche, Fatemeh
    Bijanzadeh, Hamid Reza
    CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (10) : 1953 - 1956
  • [25] One-pot synthesis of 2-acylimino-3-arylthiazoline derivatives in aqueous media
    Wang, Xicun
    Wang, Fang
    Quan, Zhengjun
    Zhang, Zhang
    Wang, Mangang
    SYNTHETIC COMMUNICATIONS, 2006, 36 (17) : 2453 - 2460
  • [26] A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media
    Chawla, Ruchi
    Kapoor, Ritu
    Singh, Atul K.
    Yadav, Lal Dhar S.
    GREEN CHEMISTRY, 2012, 14 (05) : 1308 - 1313
  • [27] Visible Light and Aqueous Ethanol Synergy: An Efficient One-Pot Route for the Synthesis of Spiropyran Derivatives
    Rai, Pragati
    Rahila
    Sagir, Hozeyfa
    Siddiqui, I. R.
    CHEMISTRYSELECT, 2016, 1 (15): : 4550 - 4553
  • [28] One-Pot Multicomponent Synthesis of Novel Spiro-(1,8)-Naphthyridine Derivatives in PEG-400
    Asilpour, Fatemeh
    Saberi, Dariush
    Hasaninejad, Alireza
    CHEMISTRYSELECT, 2023, 8 (39):
  • [29] A Facile, One-Pot Synthesis of Functionalized Spiro-Oxindoles via Vinylogous Aldol Reaction of Vinyl Malononitriles with Isatin Derivatives in Aqueous Media
    Babu, Thelagathoti Hari
    Karthik, K.
    Perumal, Paramasivan T.
    SYNLETT, 2010, (07) : 1128 - 1132
  • [30] One-Pot Electrochemical Synthesis of Fused Indole Derivatives Containing Active Hydroxyl Groups in Aqueous Medium
    Zeng, Cheng-Chu
    Liu, Fu-Jian
    Ping, Da-Wei
    Hu, Li-Ming
    Cai, Yuan-Li
    Zhong, Ru-Gang
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16): : 6386 - 6389