INTRAMOLECULAR HECK INSERTION OF A DIENE-ALLYLIC AMINATION CASCADE TO SYNTHESIZE A 2-ALKENYL-3,4-FUSED INDOLE STRUCTURE

被引：1

作者：

Kurihara, Takahito ^{[1
]}

Ueda, Jun ^{[1
]}

Tanaka, Yuito ^{[1
]}

Nakajima, Masaya ^{[1
]}

Harada, Shingo ^{[1
]}

Nemoto, Tetsuhiro ^{[1
,2
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

来源：

HETEROCYCLES | 2018年 / 97卷 / 02期

关键词：

3,4-FUSED TRICYCLIC INDOLES; HYDROARYLATION; COMBINATION; CYCLIZATION; ANNULATION; ALKYNE;

D O I：

10.3987/COM-18-S(T)62

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodoanilines bearing a diene side-chain at the 3-position were converted to tricyclic fused indole derivatives under palladium catalysis. This cascade reaction proceeds through an intramolecular Heck insertion of the diene, followed by an allylic amination reaction sequence. Experimental and computational studies indicated that eta(3) pi-allylpalladium complex-mediated substitution was operative for the latter cyclization.

引用

页码：1175 / 1190

页数：16

共 13 条

[1] A Pd(0)-Mediated Indole (Macro)cyclization Reaction
Breazzano, Steven P.
Poudel, Yam B.
Boger, Dale L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1600 - 1606
[2] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
Cacchi, S
Fabrizi, G
[J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
[3] PREPARATION OF OPIUM-ALKALOIDS BY PALLADIUM-CATALYZED BIS-CYCLIZATIONS - FORMAL TOTAL SYNTHESIS OF MORPHINE
HONG, CY
OVERMAN, LE
[J]. TETRAHEDRON LETTERS, 1994, 35 (21) : 3453 - 3456
[4] Synthetic Study of Dragmacidin E: Construction of the Core Structure Using Pd-Catalyzed Cascade Cyclization and Rh-Catalyzed Aminoacetoxylation
Inoue, Naoya
Nakano, Shun-ichi
Harada, Shingo
Hamada, Yasumasa
Nemoto, Tetsuhiro
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05) : 2787 - 2793
[5] Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety
Kochanowska-Karamyan, Anna J.
Hamann, Mark T.
[J]. CHEMICAL REVIEWS, 2010, 110 (08) : 4489 - 4497
[6] Intramolecular Dearomatizing [3+2] Annulation of α-Imino Carbenoids with Aryl Rings Furnishing 3,4-Fused Indole Skeletons
Miura, Tomoya
Funakoshi, Yuuta
Murakami, Masahiro
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (06) : 2272 - 2275
[7] Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene-Allylic Amination Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles
Nakano, Shun-ichi
Inoue, Naoya
Hamada, Yasumasa
Nemoto, Tetsuhiro
[J]. ORGANIC LETTERS, 2015, 17 (11) : 2622 - 2625
[8] Intramolecular Fischer Indole Synthesis and its Combination with an Aromatic [3,3]-Sigmatropic Rearrangement for the Preparation of Tricyclic Benzo[cd]indoles
Park, In-Keol
Park, Jun
Cho, Cheon-Gyu
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) : 2496 - 2499
[9] Intramolecular Fischer Indole Synthesis in Combination with Alkyne Hydroarylation: Synthesis of Tetracyclic Chromeno-indoles
Park, Jun
Kim, Sun-Young
Kim, Ji-Eun
Cho, Cheon-Gyu
[J]. ORGANIC LETTERS, 2014, 16 (01) : 178 - 181
[10] Intramolecular Larock Indole Synthesis: Preparation of 3,4-Fused Tricyclic Indoles and Total Synthesis of Fargesine
Shan, Dong
Gao, Yan
Jia, Yanxing
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) : 4902 - 4905

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