Visible-Light-Induced Intermolecular Dearomative Cyclization of 2-Bromo-1,3-dicarbonyl Compounds and Alkynes: Synthesis of Spiro[4.5]deca-1,6,9-trien-8-ones

被引：39

作者：

Dong, Wuheng ^{[1
]}

Yuan, Yao ^{[1
]}

Gao, Xiaoshuang ^{[1
]}

Keranmu, Miladili ^{[1
]}

Li, Wanfang ^{[1
]}

Xie, Xiaomin ^{[1
]}

Zhang, Zhaoguo ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ASYMMETRIC DEAROMATIZATION; ALLYLIC DEAROMATIZATION; N-BENZYLACRYLAMIDES; PHOTOREDOX CATALYSIS; RADICAL CYCLIZATION; ALKYLATION; ACCESS; TRIFLUOROMETHYLATION; SPIROCYCLIZATION; ALKENYLATION;

D O I：

10.1021/acs.orglett.8b02463

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

visible-light-induced photocatalytic intermolecular dearomative cyclization of 2-bromo-1,3-dicarbonyl compounds and alkynes afforded biologically important spirocarbocycle structures in moderate to good yields via a S-exo-dig radical cyclization under mild reaction conditions. A 5.0 mmol scale dearomatization reaction proceeded smoothly with 95% yield even when the catalyst loading was reduced to 0.1 mol %, suggesting that this method was suitable for large-scale synthesis.

引用

页码：5762 / 5765

页数：4

共 21 条

[1] Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-ones
Dong, Wuheng
Yuan, Yao
Xie, Xiaomin
Zhang, Zhaoguo
ORGANIC LETTERS, 2020, 22 (02) : 528 - 532
[2] A simple and efficient route for the synthesis of novel isoxazolyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Rajanarendar Eligeti
Rama Krishna Saini
Raju Samala
Journal of the Iranian Chemical Society, 2013, 10 : 653 - 658
[3] A simple and efficient route for the synthesis of novel isoxazolyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Eligeti, Rajanarendar
Saini, Rama Krishna
Samala, Raju
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (04) : 653 - 658
[4] Synthesis and Rearrangement of 1-Substituted 3,3,7-Trimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Yu. V. Nifontov
V. A. Glushkov
O. G. Ausheva
Yu. V. Shklyaev
Russian Journal of Organic Chemistry, 2002, 38 : 1386 - 1387
[5] Synthesis and rearrangement of 1-substituted 3,3,7-trimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Nifontov, YV
Glushkov, VA
Ausheva, OG
Shklyaev, YV
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (09) : 1386 - 1387
[6] Spirocyclohexadienones. 6. Three-component synthesis of 1-R-3,3-dimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Glushkov, VA
Ausheva, OG
Shurov, SN
Shklyaev, YV
RUSSIAN CHEMICAL BULLETIN, 2002, 51 (05) : 894 - 896
[7] Synthesis of 1-Substituted 2-Azaspiro[4.5]deca-6,9-dien-8-ones and 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones by Condensation of 2,6-Dimethylphenol with Isobutyraldehyde and Nitriles
Rozhkova, Yu. S.
Khmelevskaya, K. A.
Shklyaev, Yu. V.
Ezhikova, M. A.
Kodess, M. I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (01) : 69 - 77
[8] Spirocyclohexadienones. 6. Three-component synthesis of 1-R-3,3-dimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
V. A. Glushkov
O. G. Ausheva
S. N. Shurov
Yu. V. Shklyaev
Russian Chemical Bulletin, 2002, 51 : 894 - 896
[9] Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-dien-8-ones and 2-azaspiro[4.5]deca-1,6,9-trien-8-ones by condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles
Yu. S. Rozhkova
K. A. Khmelevskaya
Yu. V. Shklyaev
M. A. Ezhikova
M. I. Kodess
Russian Journal of Organic Chemistry, 2012, 48 : 69 - 77
[10] Spirocyclohexadienones - 4. Synthesis and dienone-phenolic rearrangement of 1-R-3,3-dialkyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
Ausheva, OG
Glushkov, VA
Shurov, SN
Shklyaev, YV
RUSSIAN CHEMICAL BULLETIN, 2001, 50 (09) : 1648 - 1656

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