Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines

被引：38

作者：

Baek, Yonghyeon ^{[1
]}

Maeng, Chanyoung ^{[1
]}

Kim, Hyunseok ^{[1
]}

Lee, Phil Ho ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem, Chunchon 24341, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

DIAZO OXIME ETHERS; RING EXPANSION; ONE-POT; DERIVATIVES; 3-DIAZOINDOLIN-2-IMINES; TRANSANNULATION; 2H-AZIRINES; INDOLES; 1,2,3-THIADIAZOLES; PYRIDOTRIAZOLES;

D O I：

10.1021/acs.joc.8b00115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective synthetic method for the preparation of indolopyrazines was demonstrated through a sequential Rh-catalyzed formal [3+3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint.

引用

页码：2349 / 2360

页数：12

共 50 条

[41] Rhodium-catalyzed synthesis of N-substituted 3-acylpyrroles from enaminones and vinylene carbonate
Ma, Jian-Bo
Yin, Yi-Mai
Hu, Xing-Mei
Shao, Bi-Na
Huang, Kun
Zhao, Qing-Sheng
Yan, Sheng-Jiao
ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (02): : 544 - 552
[42] Lewis Acid Catalyzed Formal Intramolecular [3+3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons
Ma, Weiwei
Fang, Jie
Ren, Jun
Wang, Zhongwen
ORGANIC LETTERS, 2015, 17 (17) : 4180 - 4183
[43] Synthesis of Benzofurans via Tandem Rhodium-Catalyzed C(sp3)-H Insertion and Copper-Catalyzed Dehydrogenation
Li, Lin
Xia, Xiao-Han
Wang, Yong
Bora, Pranjal P.
Kang, Qiang
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2089 - 2097
[44] Straightforward regioselective construction of 3,4-dihydro-2H-1,4-thiazine by rhodium catalysed [3+3] cycloaddition of thiirane with 1-sulfonyl-1,2,3-triazole: a pronounced acid additive effect
Lu, Xiao-Long
Liu, Ya-Ting
Wang, Qing-Xia
Shen, Mei-Hua
Xu, Hua-Dong
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06): : 725 - 729
[45] Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides
Gopula, Balraj
Yang, Shu-Han
Kuo, Ting-Shen
Hsieh, Jen-Chieh
Wu, Ping-Yu
Henschke, Julian P.
Wu, Hsyueh-Liang
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (31) : 11050 - 11055
[46] Palladium(II)-Catalyzed Formal [3+2] Cycloaddition of Aziridines with 3-Substituted Indoles: Synthesis of Enantioenriched Pyrroloindolines
Huang, You-ming
Zheng, Chang-wu
Pan, Lu
Jin, Qiao-wen
Zhao, Gang
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 10710 - 10718
[47] Rapid and Efficient Construction of Indolizino[3,4,5-ab]isoindole Skeletons by a Rhodium-Catalyzed Tandem Reaction
Liu, Chang
Wu, Shaonan
Sun, Wan
Meng, Haifang
Xing, Siyang
Zhu, Bolin
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (01) : 68 - 72
[48] Synthesis of Fluorenes via Tandem Copper-Catalyzed [3+2] Cycloaddition and Rhodium-Catalyzed Denitrogenative Cyclization in a 5-Exo Mode from 2-Ethynylbiaryls and N-Sulfonyl Azides in One Pot
Seo, Boram
Jeon, Woo Hyung
Kim, Jaeeun
Kim, Sunghwa
Lee, Phil Ho
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) : 722 - 732
[49] Rhodium-catalyzed synthesis of 2,3-Disubstituted N-methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins
Kuruba, Bharath Kumar
Vasanthkumar, Samuel
Emmanuvel, Lourdusamy
TETRAHEDRON, 2017, 73 (22) : 3093 - 3098
[50] Enantioselective Synthesis of Dihydropyrazolo[3,4-b]pyridin-6-ones via N-Heterocyclic Carbene Catalyzed [3+3] Cycloaddition of a-Bromoenals with 5-Aminopyrazoles
Li, Yarui
Huang, Xiaoxia
He, Jieyin
Peng, Shiyong
Wang, Jian
Lang, Ming
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (04) : 490 - 495

← 1 2 3 4 5 →