Lewis acid free synthesis of 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-triones promoted by 1,1,1,3,3,3-hexafluoro-2-propanol

被引:60
|
作者
Maleki, Behrooz [1 ]
Ashrafi, Samaneh Sedigh [1 ]
Tayebee, Reza [1 ]
机构
[1] Hakim Sabzevari Univ, Dept Chem, Sabzevar 9617976487, Iran
来源
RSC ADVANCES | 2014年 / 4卷 / 78期
关键词
ONE-POT SYNTHESIS; EFFICIENT CATALYST; 3-COMPONENT SYNTHESIS; FLUORINATED ALCOHOLS; POLYMERIC CATALYST; METAL-FREE; DERIVATIVES; PHTHALAZINE; OXIDATION;
D O I
10.1039/c4ra06768a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient, environmentally friendly and efficient procedure for the synthesis 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione derivatives has been developed via multi-component and one-pot reactions of various aldehydes with cyclic 1,3-diketones and phthalhydrazide 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). In simple and mild reaction conditions, the use of HFIP is explored as an easy workup and a green catalyst for the one-pot three-component synthesis of 3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H, 13H)-triones. Thus, this practical method is developed as a notable medium for these derivatives via a multicomponent reaction.
引用
收藏
页码:41521 / 41528
页数:8
相关论文
共 50 条
  • [31] Synthesis of 2H-Indazolo[2,1-b]phthalazine-1,6,11(13H)-trione Derivatives Using Wet Cyanuric Chloride under Solvent-Free Condition
    Wang, Xiao
    Ma, Wei-Wei
    Wu, Li-Qiang
    Yan, Fu-Lin
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2010, 57 (6B) : 1341 - 1345
  • [32] Metal-Free Synthesis of Chlorinated β-Amino Ketones via an Unexpected Reaction of Imines with Arylacetylenes in 1,1,1,3,3,3-Hexafluoro-2-propanol
    Kushwaha, Khushbu
    Pinter, Balazs
    Shehzadi, Syeda A.
    Malakar, Chandi C.
    Velde, Christophe M. L. Vande
    de Proft, Frank
    Tehrani, Kourosch Abbaspour
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) : 41 - 49
  • [33] SYNTHESIS, SALUDIURETIC, AND ANTIHYPERTENSIVE ACTIVITY OF 6,7-DISUBSTITUTED 1(2H)- AND 3,4-DIHYDRO-1(2H)-PHTHALAZINONES
    CHERKEZ, S
    HERZIG, J
    YELLIN, H
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) : 947 - 959
  • [34] 1,1,1,3,3,3-hexafluoro-2-propanol as a reusable media: Green and catalyst-free synthesis of pyrano[2,3-d]pyrimidine scaffolds
    Mohamadpour, Farzaneh
    JOURNAL OF CHEMICAL SCIENCES, 2024, 137 (01)
  • [35] SYNTHESIS OF CHALCOGENO LACTONES .2. 3,4-DIHYDRO-1H-2-BENZOTHIIN-3-ONE, "3,4-DIHYDRO-1H-2-BENZOSELENIN-3-ONE AND 3,4-DIHYDRO-1H-2-BENZOTELLURIN-3-ONE
    LEMAIRE, C
    LUXEN, A
    CHRISTIAENS, L
    GUILLAUME, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) : 811 - 812
  • [36] Synthesis of 3,4-dihydro-2H-pyrido[1,2-b]isoindol-1-one and 3,4-dihydro-2H-pyrido[1,2-b]pyrrolidin-1-one functionalized at the C-6 position by an intramolecular Horner-Wadsworth-Emmons reaction
    Gourves, JP
    Couthon, H
    Sturtz, G
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (12) : 3489 - 3493
  • [37] SYNTHESIS OF A NEW NITROGEN HETEROCYCLE - 2H,3H-BENZIMIDAZO-(1,2-B)-OXAZOLE
    BENIGNI, F
    TREVISAN, L
    FARMACO-EDIZIONE SCIENTIFICA, 1974, 29 (12): : 936 - 940
  • [38] 3,3-Dimethyl-5-phenyl-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione
    Fun, Hoong-Kun
    Teh, Jeannie Bee-Jan
    Liu, Yun
    Xu, Jian-Hua
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3146 - U2975
  • [39] Efficient one-pot three-component synthesis of 2H-indazole [2,1-b]phthalazine-1,6,11(13H)-triones at room temperature
    Pisal, Parshuram M.
    Kamble, Vinod T.
    Varala, Ravi
    Gujarathi, Pradip B.
    ORGANIC COMMUNICATIONS, 2020, 13 (04) : 194 - 201
  • [40] Solvolysis of 3,4-dihalogeno-3,4-dihydro-2H-naphtho[1,2-b]pyran and 1,2-dihalogeno-2,3-dihydro-1H- naphtho[2,1-b]pyrans
    Derrick, IAR
    Livingstone, R
    McGreevy, BJ
    JOURNAL OF CHEMICAL RESEARCH-S, 1999, (11): : 640 - 641A