Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine

被引：88

作者：

Inamoto, Kiyofumi ^{[1
]}

Katsuno, Mika

Yoshino, Takashi

Arai, Yukari

Hiroya, Kou

Sakamoto, Takao

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, 21st Century COE Program, Comprehens Res & Educ Ctr Planning Drug Dev & Cli, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 12期

关键词：

palladium; animation; hydrazone; indazole; benzoisoxazole; nigellicine;

D O I：

10.1016/j.tet.2007.01.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2695 / 2711

页数：17

共 55 条

[1] PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380

[2] REACTION OF AZOARENES WITH TRIBUTYLTIN HYDRIDE [J].

ALBERTI, A ;

BEDOGNI, N ;

BENAGLIA, M ;

LEARDINI, R ;

NANNI, D ;

PEDULLI, GF ;

TUNDO, A ;

ZANARDI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :607-613

[3] Palladium-catalyzed amination of aryl nonaflates [J].

Anderson, KW ;

Mendez-Perez, M ;

Priego, J ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9563-9573

[4]

[Anonymous], J MED CHEM

[5]

ARDAKANI MA, 1979, SYNTHESIS-STUTTGART, P308

[6] REDUCTION OF NITRO-COMPOUNDS AND NITROSO-COMPOUNDS BY TERVALENT PHOSPHORUS REAGENTS .11. KINETIC STUDY OF EFFECTS OF VARYING REAGENT AND NITRO-COMPOUND IN CONVERSION OF ORTHO-NITROBENZYL-IDENEAMINES TO 2-SUBSTITUTED INDAZOLES [J].

ARMOUR, MA ;

CADOGAN, JIG ;

GRACE, DSB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (11) :1185-1189

[7] Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: a mild and flexible strategy to design 2-aza tryptamines [J].

Arnautu, A ;

Collot, V ;

Ros, JC ;

Alayrac, C ;

Witulski, B ;

Rault, S .

TETRAHEDRON LETTERS, 2002, 43 (15) :2695-2697

[8]

Atta-ur-Rahman Malik S., 1985, TETRAHEDRON LETT, V26, P2759

[9] KINETICS OF CYCLIZATION OF OMICRON-HALOBENZOPHENONE OXIMES TO 3-PHENYL-1,2-BENZISOXAZOLE [J].

BUNNETT, JF ;

YIH, SY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (18) :3805-&

[10] Intramolecular C-N bond formation in the reductive elimination of ortho-palladated arylhydrazones of acetophenone [J].

Carbayo, A ;

Cuevas, JV ;

García-Herbosa, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 658 (1-2) :15-20

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