Transition-Metal-Free Synthesis of Substituted Pyridines via Ring Expansion of 2-Allyl-2H-azirines

被引：93

作者：

Jiang, Yaojia ^{[1
]}

Park, Cheol-Min ^{[3
]}

Loh, Teck-Peng ^{[1
,2
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637616, Singapore

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[3] UNIST, Dept Chem, UNIST Gil 50, Ulsan 689798, South Korea

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 13期

关键词：

HIGHLY FUNCTIONALIZED PYRIDINES; DE-NOVO SYNTHESIS; POLYSUBSTITUTED PYRIDINES; REGIOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; DIELS-ALDER; 2H-AZIRINES; ROUTE; ALKYNES; DERIVATIVES;

D O I：

10.1021/ol501010k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy to open the 2-allyl-2H-azirines by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) promotion in metal-free conditions affording 1-azatrienes that in situ electrocyclize to the pyridines in good to excellent yields is reported. 1:22 The reaction displays a broad substrate scope and good tolerance to a variety of substituents including aryl, alkyl, and heterocyclic groups. In addition, one-pot synthesis of pyridines from oximes via in situ formation of 2H-azirines was achieved.

引用

页码：3432 / 3435

页数：4

共 50 条

[31] Transition-Metal-Free Synthesis of 2-Arylimidazolones via Cascade Reaction between Arynes and α,α′-Disubstituted α-Isocyanoacetamides
Gesu, Alessandro
Pozzoli, Claudio
Torre, Enza
Aprile, Silvio
Pirali, Tracey
[J]. ORGANIC LETTERS, 2016, 18 (09) : 1992 - 1995
[32] Transition-metal-free radical difluorobenzylation/cyclization of unactivated alkenes: access to ArCF2-substituted ring-fused quinazolinones
Yuan, Jin-Wei
Zhang, Mei-Yue
Liu, Yan
Hu, Wen-Yu
Yang, Liang-Ru
Xiao, Yong-Mei
Diao, Xiao-Qiong
Zhang, Shou-Ren
Mao, Jian
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (48) : 9722 - 9733
[33] Metal-Free Synthesis of Fully Substituted Pyridines via Ring Construction Based on the Domino Reactions of Enaminones and Aldehydes
Wan, Jie-Ping
Jing, Yanfeng
Hu, Changfeng
Sheng, Shouri
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6826 - 6831
[34] Transition-Metal-Free Silylation of Unactivated C(sp2)-H Bonds with tert-Butyl-Substituted Silyldiazenes
Neil, Baptiste
Lucien, Franck
Fensterbank, Louis
Chauvier, Clement
[J]. ACS CATALYSIS, 2021, 11 (21): : 13085 - 13090
[35] Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates
Seo, Jeong Hoon
Ko, Haye Min
[J]. TETRAHEDRON LETTERS, 2018, 59 (07) : 671 - 674
[36] Transition-metal-free synthesis of quinolines from 2-nitrobenzyl alcohol in water
Zhu, Meijuan
Wang, Chao
Tang, Weijun
Xiao, Jianliang
[J]. TETRAHEDRON LETTERS, 2015, 56 (48) : 6758 - 6761
[37] SYNTHESIS AND PROPERTIES OF SUBSTITUTED 3-AMINO-2H-AZIRINES
EREMEYEV, AV
PISKUNOVA, IP
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1990, (07): : 867 - 887
[38] Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives
Fu, Xinlei
Wu, Longhui
Guo, Xiaohua
Yang, Kai
Liu, Zhaowen
[J]. JOURNAL OF SAUDI CHEMICAL SOCIETY, 2024, 28 (04)
[39] Transition-Metal-Free Synthesis of Unsymmetrical Diaryl Tellurides via SH2 Reaction of Aryl Radicals on Tellurium
Yamamoto, Yuki
Sato, Fumiya
Chen, Qiqi
Kodama, Shintaro
Nomoto, Akihiro
Ogawa, Akiya
[J]. MOLECULES, 2022, 27 (03):
[40] Transition-Metal-Catalyzed C-H Functionalization for the Synthesis of Substituted Pyridines
Nakao, Yoshiaki
[J]. SYNTHESIS-STUTTGART, 2011, (20): : 3209 - 3219

← 1 2 3 4 5 →