A Metal-Free C-H Amination-Based Strategy for N-Amino Indole Synthesis

被引：1
作者：
Corrieri, Matteo [1 ]
De Crescentini, Lucia [1 ]
Mantellini, Fabio [1 ]
Mari, Giacomo [1 ]
Santeusanio, Stefania [1 ]
Favi, Gianfranco [1 ]
机构：
[1] Univ Urbino Carlo Bo, Dept Biomol Sci, Sect Organ Chem & Pharmaceut Technol, Via I Maggetti 24, I-61029 Urbino, PU, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 21期
关键词：
cyclization; C(sp(2))-H amination; indoles; hydrazones; hypervalent iodine(III) reagent; INTRAMOLECULAR CYCLIZATION; 1-AMINOINDOLE DERIVATIVES; ANNULATION; PIFA; ACTIVATION; CHEMISTRY; ANALOGS; AGENTS;
D O I：
10.1002/ejoc.202300242
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An oxidative cyclization of electron-rich alpha-arylhydrazones promoted by phenyliodine bis(trifluoroacetate) (PIFA) has been accomplished. This metal-free, chemoselective transformation allows to obtain synthetically and medicinally important N-amino-1H-indoles, obviating the need for pre-functionalization of substrates.
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页数：6
相关论文
共 65 条
[1]   SELECTIVE, CENTRALLY ACTING SEROTONIN 5-HT2 ANTAGONISTS .2. SUBSTITUTED 3-(4-FLUOROPHENYL)-1H-INDOLES [J].
ANDERSEN, K ;
PERREGAARD, J ;
ARNT, J ;
NIELSEN, JB ;
BEGTRUP, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (26) :4823-4831
[2]   Synthesis of carbazolones and 3-acetylindoles via oxidative C-N bond formation through PIFA-mediated annulation of 2-aryl enaminones [J].
Ban, Xu ;
Pan, Yan ;
Lin, Yingfu ;
Wang, Songqing ;
Du, Yunfei ;
Zhao, Kang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) :3606-3609
[3]  
Belley M, 2001, SYNLETT, P222
[4]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[5]   Zn(II)-Catalyzed Addition of Aromatic/Heteroaromatic C(sp2)-H to Azoalkenes: A Polarity-Reversed Arylation of Carbonyl Compounds [J].
Ciccolini, Cecilia ;
De Crescentini, Lucia ;
Mantellini, Fabio ;
Santeusanio, Stefania ;
Favi, Gianfranco .
ORGANIC LETTERS, 2019, 21 (11) :4388-4391
[6]   A NEW SYNTHESIS OF QUINOLINE DERIVATIVES [J].
CLEMENTE, DTV ;
LOBO, AM ;
PRABHAKAR, S ;
MARCELOCURTO, MJ .
TETRAHEDRON LETTERS, 1994, 35 (13) :2043-2046
[7]   Synthesis of Azacarbolines via PhIO2-Promoted Intramolecular Oxidative Cyclization of α-Indolylhydrazones [J].
Corrieri, Matteo ;
De Crescentini, Lucia ;
Mantellini, Fabio ;
Mari, Giacomo ;
Santeusanio, Stefania ;
Favi, Gianfranco .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (24) :17918-17929
[8]   Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles [J].
Dahiya, Anjali ;
Sahoo, Ashish Kumar ;
Chakraborty, Nikita ;
Das, Bubul ;
Patel, Bhisma K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (10) :2005-2027
[9]   Reactions promoted by hypervalent iodine reagents and boron Lewis acids [J].
Dasgupta, Ayan ;
Thiehoff, Christian ;
Newman, Paul D. ;
Wirth, Thomas ;
Melen, Rebecca L. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) :4852-4865
[10]   Oxidative Coupling of N-Methoxyamides and Related Compounds toward Aromatic Hydrocarbons by Designer μ-Oxo Hypervalent Iodine Catalyst [J].
Dohi, Toshifumi ;
Sasa, Hirotaka ;
Dochi, Mio ;
Yasui, Chihiro ;
Kita, Yasuyuki .
SYNTHESIS-STUTTGART, 2019, 51 (05) :1185-1195
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