Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquinolines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation

被引：27

作者：

Brahma, Kaushik ^{[1
]}

Achari, Basudeb ^{[1
]}

Chowdhury, Chinmay ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Div Chem, CSIR, 4 Raja SC Mullick Rd, Kolkata 700032, India

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 04期

关键词：

1,2,3-triazoles; nitrogen heterocycles; intramolecular reactions; azide-alkyne cycloaddition; bis-heteroannulations; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; BIOLOGICAL-ACTIVITY; DIRECT ARYLATIONS; INHIBITORS; ANTAGONISTS; RECEPTOR; TRIAZOLE; ANALOGS; ALKYNES;

D O I：

10.1055/s-0032-1316839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types.

引用

页码：545 / 555

页数：11

共 65 条

[41] The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence [J].

Malachowski, William P. ;

Paul, Tapas ;

Phounsavath, Sophia .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) :6792-6796

[42] Triazole Inhibitors of Cryptosporidium parvum Inosine 5′-Monophosphate Dehydrogenase [J].

Maurya, Sushil K. ;

Gollapalli, Deviprasad R. ;

Kirubakaran, Shivapriya ;

Zhang, Minjia ;

Johnson, Corey R. ;

Benjamin, Nicole N. ;

Hedstrom, Lizbeth ;

Cuny, Gregory D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (15) :4623-4630

[43] The growing applications of click chemistry [J].

Moses, John E. ;

Moorhouse, Adam D. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (08) :1249-1262

[44] Click chemistry: Versatility and control in the hands of materials scientists [J].

Nandivada, Himabindu ;

Jiang, Xuwei ;

Lahann, Joerg .

ADVANCED MATERIALS, 2007, 19 (17) :2197-2208

[45] Novel tricyclic pyrazole BRAF inhibitors with imidazole or furan central scaffolds [J].

Niculescu-Duvaz, Dan ;

Niculescu-Duvaz, Ion ;

Suijkerbuijk, Bart M. J. M. ;

Menard, Delphine ;

Zambon, Alfonso ;

Nourry, Arnaud ;

Davies, Lawrence ;

Manne, Helen A. ;

Friedlos, Frank ;

Ogilvie, Lesley ;

Hedley, Douglas ;

Takle, Andrew K. ;

Wilson, David M. ;

Pons, Jean-Francois ;

Coulter, Tom ;

Kirk, Ruth ;

Cantarino, Neus ;

Whittaker, Steven ;

Marais, Richard ;

Springer, Caroline J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (18) :6934-6952

[46] Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp. [J].

Oku, N ;

Matsunaga, S ;

van Soest, RWM ;

Fusetani, N .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08) :1136-1139

[47] Synthesis and antiviral activity of novel anti-VZV 5-substituted uracil nucleosides with a cyclopropane sugar moiety [J].

Onishi, T ;

Mukai, C ;

Nakagawa, R ;

Sekiyama, T ;

Aoki, M ;

Suzuki, K ;

Nakazawa, H ;

Ono, N ;

Ohmura, Y ;

Iwayama, S ;

Okunishi, M ;

Tsuji, T .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (02) :278-282

[48] Identification and characterization of inhibitors of West Nile virus [J].

Puig-Basagoiti, Francesc ;

Qing, Min ;

Dong, Hongping ;

Zhang, Bo ;

Zou, Gang ;

Yuan, Zhiming ;

Shi, Pei-Yong .

ANTIVIRAL RESEARCH, 2009, 83 (01) :71-79

[49] 5-[1′-(2′-N-arylsulfonyl-1′,2′,3′,4′-tetrahydroisoquinolyl) ]-4,5-dihydro-2(3H)-furanones:: Positive allosteric modulators of the GABAA receptor with a new mode of action [J].

Razet, R ;

Thomet, U ;

Furtmüller, R ;

Chiaroni, A ;

Sigel, E ;

Sieghart, W ;

Dodd, RH .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (23) :4363-4366

[50] Controlled double-bond migration in palladium-catalyzed intramolecular arylation of enamidines [J].

Ripa, L ;

Hallberg, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7147-7155

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