One-Pot Ring-Closing Metathesis/1,3-Dipolar Cycloaddition through Assisted Tandem Ruthenium Catalysis: Synthesis of a Dye with Isoindolo[2,1-a]quinoline Structure

被引：39

作者：

Arisawa, Mitsuhiro ^{[1
,2
,3
]}

Fujii, Yuki ^{[1
,2
,3
]}

Kato, Hiroshige ^{[1
,2
,3
]}

Fukuda, Hayato ^{[1
,2
,3
]}

Matsumoto, Takashi ^{[1
,2
,3
]}

Ito, Mika ^{[1
,2
,3
]}

Abe, Hiroshi ^{[1
,2
,3
]}

Ito, Yoshihiro ^{[1
,2
,3
]}

Shuto, Satoshi ^{[1
,2
,3
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Rigaku Corp, Xray Res Lab, Akishima, Tokyo 1968666, Japan

[3] RIKEN, Adv Sci Inst, Nano Med Engn Lab, Wako, Saitama 3510198, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 03期

基金：

日本科学技术振兴机构;

关键词：

cycloaddition; domino reactions; dyes; pigments; metathesis; ruthenium; OLEFIN METATHESIS; SEQUENCE; CARBENE; ISOMERIZATION; ALKYNES; CYCLOISOMERIZATION; HETEROCYCLES; NITROGEN; HYDRIDE; COMPLEX;

D O I：

10.1002/anie.201206765

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The one-pot tandem reaction of N-alkyl-N-allyl-2-vinylaniline derivatives with benzo- or naphthoquinones and a ruthenium-alkylidene catalyst leads to isoindolo[2,1-a]quinolines in a variety of colors, which can be altered by exchanging the substituent on the core heterocycle (see scheme). This reaction offers a new synthetic method for π-conjugated small molecules from simple aniline derivatives. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1003 / 1007

页数：5

共 10 条

[1] One-Pot Olefin Isomerization/Aliphatic Enamine Ring-Closing Metathesis/Oxidation/1,3-Dipolar Cycloaddition for the Synthesis of Isoindolo[1,2-a]isoquinolines
Fujii, Yuki
Takehara, Tsunayoshi
Suzuki, Takeyuki
Fujioka, Hiromichi
Shuto, Satoshi
Arisawa, Mitsuhiro
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) : 4055 - 4062
[2] One-Pot Ring-Closing Metathesis (RCM)/Oxidation by an Assisted Tandem Ruthenium Catalysis for the Synthesis of 2-Quinolones
Kato, Hiroshige
Ishigame, Tatsuya
Oshima, Nobuhiro
Hoshiya, Naoyuki
Shimawaki, Ken
Arisawa, Mitsuhiro
Shuto, Satoshi
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) : 2676 - 2680
[3] Absorption, fluorescence, and two-photon excitation ability of 5-phenyl-13-arylisoindolo[2,1-a]quinolines prepared by one-pot reaction of ring-closing metathesis and 1,3-dipolar cycloaddition
Ramon, Avena Francisco
Wada, Yuki
Ishii, Hirokazu
Watakabe, Yuki
Tsutsumi, Motosuke
Jang, Kwangkyun
Otomo, Kohei
Qiao, Lin
Fujii, Yuki
Tsujino, Hirofumi
Tsutsumi, Yasuo
Nemoto, Tomomi
Arisawa, Mitsuhiro
[J]. DYES AND PIGMENTS, 2023, 212
[4] A novel one-pot, three-component access to hexahydropyrrolo[2,1-a]isoquinolines by an alkylation-dehydrohalogenation-1,3-dipolar cycloaddition sequence
Nyerges, M
Somfai, B
Tóth, J
Töke, L
Dancsó, A
Blaskó, G
[J]. SYNTHESIS-STUTTGART, 2005, (12): : 2039 - 2045
[5] Regioselective Synthesis of 3-Carbo-5-phosphonylpyrazoles through a One-Pot Claisen-Schmidt/1,3-Dipolar Cycloaddition/Oxidation Sequence
Martin, Anthony R.
Mohanan, Kishor
Toupet, Loic
Vasseur, Jean-Jacques
Smietana, Michael
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (17) : 3184 - 3190
[6] A one-pot synthesis and 1,3-dipolar cycloaddition of [1,2]dithiolo[4,3-b]indole-3(4H)-thiones
Konstantinova, Lidia S.
Lysov, Kirill A.
Amelichev, Stanislav A.
Obruchnikova, Natalia V.
Rakitin, Oleg A.
[J]. TETRAHEDRON, 2009, 65 (11) : 2178 - 2183
[7] One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols
Zhang, Xiao-Lan
Wei, Mei-Hong
Chen, Jun-Min
Liu, Xiao-Ling
[J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 97 - 103
[8] One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/N-alkylation (N-acylation)/Staudinger/aza-Wittig reactions
Ma, Xiaoming
Zhang, Xiaofeng
Awad, John Mark
Xie, Guoshu
Qiu, Weiqi
Zhang, Wei
[J]. GREEN CHEMISTRY, 2019, 21 (16) : 4489 - 4494
[9] Synthesis of some tetrazole fused pyrido[2,3-c]coumarin derivatives from a one-pot three-component reaction via intramolecular 1,3-dipolar cycloaddition reaction of azide to nitriles
Borah, Pallabi
Naidu, P. Seetham
Bhuyan, Pulak J.
[J]. TETRAHEDRON LETTERS, 2012, 53 (37) : 5034 - 5037
[10] One-Pot, Three-Component Synthesis of 1-(2-Hydroxyethyl)-1H-1,2,3-triazole Derivatives by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-Azido Alcohols and Terminal Alkynes under Mild Conditions in Water
Sharghi, Hashem
Hosseini-Sarvari, Mona
Moeini, Fatemeh
Khalifeh, Reza
Beni, Alireza Salimi
[J]. HELVETICA CHIMICA ACTA, 2010, 93 (03) : 435 - 449

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