Cu(OTf)2-Catalyzed Synthesis of 2,3-Disubstituted indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones

被引：80

作者：

Reddy, B. V. Subba ^{[1
]}

Reddy, M. Ramana ^{[1
]}

Rao, Y. Gopal ^{[1
]}

Yadav, J. S. ^{[1
]}

Sridhar, B. ^{[2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 03期

关键词：

4-SUBSTITUTED INDOLES; CATALYZED SYNTHESIS; FACILE SYNTHESIS; STEP SYNTHESIS; FASCAPLYSIN; DERIVATIVES; CYCLIZATION; ROUTE; 4-OXO-4,5,6,7-TETRAHYDROINDOLES; CYCLOISOMERIZATION;

D O I：

10.1021/ol303206w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.

引用

页码：464 / 467

页数：4

共 61 条

[1] Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles [J].

Alex, Karolin ;

Tillack, Annegret ;

Schwarz, Nicolle ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2304-2307

[2] MITOMYCIN ANTIBIOTICS . SYNTHETIC STUDIES .2. SYNTHESIS OF 7-METHOXYMITOSENE ANTIBACTERIAL AGENT [J].

ALLEN, GR ;

POLETTO, JF ;

WEISS, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3877-&

[3] Synthesis of 4-Acetoxyindoles and Related Derivatives by Means of Air Oxidation of 4-Oxo-4,5,6,7-tetrahydroindoles Obtained from Nitroalkenes and Cyclohexane-1,3-diones [J].

Arai, Masaki ;

Miyauchi, Yayoi ;

Miyahara, Tadashi ;

Ishikawa, Teruhiko ;

Saito, Seiki .

SYNLETT, 2009, (01) :122-126

[4] Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Parisi, LM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6213-6217

[5] The first synthesis of the benzo[b]indolo[1,2-h][1,7]naphthyridine ring system [J].

Baranova, Olga V. ;

Zhidkov, Maxim E. ;

Dubovitskii, Sergey V. .

TETRAHEDRON LETTERS, 2011, 52 (18) :2397-2398

[6] The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles:: Domino two- and three-component synthesis of indoles [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1529-1532

[7] Versatile Synthesis of 2-(Substituted phenyl)-6,7-dihydro-1H-indol-4(5H)-ones from Morita-Baylis-Hillman Acetates of 2-Oxo-2-(substituted phenyl)acetaldehyde [J].

Batchu, Harikrishna ;

Batra, Sanjay .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (15) :2935-2944

[8] From PtCl2- and acid-catalyzed to uncatalyzed cycloisomerization of 2-propargyl anilines:: Access to functionalized indoles [J].

Cariou, Kevin ;

Ronan, Baptiste ;

Mignani, Serge ;

Fensterbank, Louis ;

Malacria, Max .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (11) :1881-1884

[9] Synthesis of homofascaplysin C and indolo[2,3-a]carbazole from ditryptophans [J].

Carter, DS ;

Van Vranken, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8537-8545

[10] Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process [J].

Chen, Yu ;

Wang, Yuji ;

Sun, Zheming ;

Ma, Dawei .

ORGANIC LETTERS, 2008, 10 (04) :625-628

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