Simple and efficient synthesis of tetrahydro-β-carbolines via the Pictet-Spengler reaction in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)

被引:39
作者
Wang, Li-Na [1 ]
Shen, Su-Li [1 ]
Qu, Jin [1 ]
机构
[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSPECIFIC TOTAL-SYNTHESIS; MONOTERPENOID INDOLE ALKALOIDS; SURFACTANT-COMBINED CATALYST; FLUORINATED ALCOHOLS; MULTIDRUG-RESISTANCE; FUMITREMORGIN C; AROMATIC-AMINES; ACID CATALYST; AQUEOUS-MEDIA; TETRAHYDROISOQUINOLINES;
D O I
10.1039/c4ra03628j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) can act as both the solvent and the catalyst to promote the Pictet-Spengler reactions between tryptamine derivatives and aldehydes or activated ketones. For most substrates, removing the low boiling point HFIP by distillation directly afforded tetrahydro-beta-carbolines in high yields.
引用
收藏
页码:30733 / 30741
页数:9
相关论文
共 50 条
[41]   Pd(AcO)2 supported by 1,3,5-triazine functionalized nanoporous polymers: Efficient and recyclable heterogeneous catalysts for Suzuki-Miyaura reaction [J].
Feng, Gaofeng ;
He, Jingyao ;
Deng, Wenshu ;
Kong, Weiping .
KINETICS AND CATALYSIS, 2015, 56 (06) :703-711
[42]   Synthesis of new 2-substituted pyrazolo[5,1-b][1,3]oxazoles via Sonogashira coupling reactions in water [J].
Bakherad, Mohammad ;
Doosti, Rahele ;
Mirzaee, Mahdi ;
Jadidi, Khosro .
TETRAHEDRON, 2017, 73 (23) :3281-3287
[43]   Synthesis and Cytotoxicity of (±)-9-Hydroxy-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-2-carboxamide: An Active Component of Juglans regia [J].
Marepu, Nagaraju ;
Yeturu, Sunandamma ;
Pal, Manojit .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (09) :1806-1809
[44]   Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines via a TFA-promoted annulation of arylpropiolaldehydes and 1,2,3,4-tetrahydroisoquinolines [J].
Zhang, Yage ;
Zhao, Wenyan ;
Hou, Guoquan ;
Liu, Li ;
Li, Jian .
TETRAHEDRON LETTERS, 2023, 120
[45]   An Efficient Four-Component Approach for the Synthesis of Novel 5-Methyl-4-(2-(3-methyl-4-nitroisoxazol-5-yl)-1-arylethyl)-1H-pyrazol-3-ol Derivatives and their Antibacterial Study [J].
Muthineni, Narmada ;
Kumar, Nandigama Satish ;
Rao, L. Chandrasekhara ;
Kumar, V. Dileep ;
Misra, Sunil ;
Chowhan, L. Raju ;
Meshram, H. M. .
CHEMISTRYSELECT, 2016, 1 (14) :4197-4202
[46]   One-pot efficient pseudo-five-components synthesis of 4,4-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) at room temperature assisted by K2CO3 [J].
Banerjee, Dipanwita ;
Karmakar, Rajiv ;
Kayal, Utpal ;
Maiti, Gourhari .
SYNTHETIC COMMUNICATIONS, 2017, 47 (10) :1006-1012
[47]   A Synthetic Route to Highly Substituted 1,2,3,4-Tetrahydroisoquinolines via Yb(OTf)3-Catalyzed Diastereoselective Ring Opening of Bridged Oxazolidines: Asymmetric Synthesis of 2-Azapodophyllotoxin [J].
Srivastava, Ajay Kumar ;
Koh, Minseob ;
Park, Seung Bum .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (17) :4905-4913
[48]   Biginelli Reaction of Vicinal Diols: A New Route for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives [J].
Jagadishbabu, Narasashetty ;
Shivashankar, Kalegowda .
LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (05) :330-336
[49]   Synthesis of 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a] pyrimidin-4-one Derivatives as Antibacterial Agents [J].
Krishnamurthy, Byregowda ;
Vinaya, Kambappa ;
Rakshith, Devraj ;
Prasanna, Doddakunche Shivaramu ;
Rangappa, Kanchugarakoppal Subbegowda .
MEDICINAL CHEMISTRY, 2013, 9 (02) :240-248
[50]   Green Synthesis of 2H-Pyrano[2,3-d][1,3]thiazole-6-carbonitriles in Trifluoroethanol as an Efficient Acidic Solvent and Their Biological Activity [J].
Shabani, N. ;
Heravi, M. R. Poor ;
Babazadeh, M. ;
Ghasemi, E. ;
Amini, M. ;
Robertson, C. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (01) :115-124