Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene-Allylic Amination Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles

被引：43

作者：

Nakano, Shun-ichi ^{[1
]}

Inoue, Naoya ^{[1
]}

Hamada, Yasumasa ^{[1
]}

Nemoto, Tetsuhiro ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 11期

关键词：

FUNCTIONALLY-SUBSTITUTED ARYL; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; (+)-LYSERGIC ACID; VINYLIC IODIDES; AMINO ALLENES; DRAGMACIDIN-E; CORE; ACTIVATION; STRATEGY;

D O I：

10.1021/acs.orglett.5b00973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an alleneallylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5-10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 degrees C, producing 3,4-fused tricyclic 3-alkylidene indoline derivatives in moderate to excellent yield. The reaction products were divergently transformed into three types of 3,4-fused tricyclic indole derivatives, successfully demonstrating the versatile properties of the reaction products.

引用

页码：2622 / 2625

页数：4

共 16 条

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[3] Platinum-Catalyzed Friedel-Crafts-Type C-H Coupling-Allylic Amination Cascade to Synthesize 3,4-Fused Tricyclic Indoles
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[10] Rh(III)-Catalyzed Intramolecular Redox-Neutral or Oxidative Cyclization of Alkynes: Short, Efficient Synthesis of 3,4-Fused Indole Skeletons
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