Synthesis of Pyridin-2(1H)-imines via the Transformation of Conjugated Ynones

被引：0

作者：

Yang, Weiguang ^{[1
,2
]}

Li, Guanrong ^{[1
]}

Huang, Zixin ^{[1
]}

Wang, Chen ^{[2
]}

Li, Hang ^{[2
]}

Zhou, Zitong ^{[1
]}

Mei, Shuangxi ^{[2
]}

Deng, Lu-Ming ^{[1
]}

机构：

[1] Guangdong Med Univ, Sch Ocean & Trop Med, Zhanjiang 524023, Guangdong, Peoples R China

[2] Southern Marine Sci & Engn Guangdong Lab Zhanjiang, Zhanjiang 524023, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 12期

关键词：

N-ARYLATION; QUINOLINE;

D O I：

10.1021/acs.joc.4c01071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugated ynones represent an important class of reactive species, useful synthetic intermediates, and synthons. However, the reactivity and synthetic applications of ynones are usually focused on the transformation of mono- or dual-functional groups. Herein, we developed a straightforward synthesis of pyridin-2(1H)-imines from the transformation of conjugated ynones. This cascade process probably began with a Michael addition of ynones and 2-aminopyridines, further underwent an intramolecular cyclization to generate the N,O-bidentate intermediates, and finally reacted with sulfonyl azides giving the pyridin-2(1H)-imines with accompanying loss of diazo.

引用

页码：9139 / 9143

页数：5

共 50 条

[1] Synthesis of Pyridin-2(1H)-one Derivatives via Enamine Cyclization
Chikhalikar, Sandip
Bhawe, Vijay
Ghotekar, Bhausaheb
Jachak, Madhukar
Ghagare, Maruti
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10): : 3829 - 3836
[2] Synthesis of chalcones on the basis of Pyridin-2(1H)-one
Kalashnikov, V. V.
Kalashnikova, I. P.
Shestov, V. I.
[J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (06) : 1247 - 1252
[3] Synthesis of chalcones on the basis of Pyridin-2(1H)-one
V. V. Kalashnikov
I. P. Kalashnikova
V. I. Shestov
[J]. Russian Journal of General Chemistry, 2008, 78 : 1247 - 1252
[4] Novel synthesis of condensed pyridin-2(1H)-one and pyrimidine derivatives
Soliman, AMM
Khodairy, A
Ahmed, EA
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (04) : 649 - 665
[5] Synthesis and characterization of new N-alkylated pyridin-2(1H)-ones
Sharma, Atul Kumar
Yadav, Preeti
Chand, Karam
Sharma, Sunil K.
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2016, 55 (04): : 492 - 500
[6] Synthesis of Pyridin-2(1H)-one Derivatives: Temperature-Dependent Selectivity
Chikhalikar, Sandip
Bhawe, Vijay
Jachak, Madhukar
Ghagare, Maruti
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (30) : 6085 - 6091
[7] SYNTHESIS OF PYRIDIN-2(1H)-ONES BY THE INTRAMOLECULAR CYCLIZATION OF AMIDES OF β-ENAMINO KETONES
Goncharov, D. S.
Kostuchenko, A. S.
Fisyuk, A. S.
[J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 793 - 795
[8] Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives
Seixas, Raquel S. G. R.
Ribeiro, Gustavo C.
Guieu, Samuel
Silva, Artur M. S.
[J]. CHEMISTRYSELECT, 2016, 1 (02): : 318 - 322
[9] Vilsmeier Reaction of Enaminones: Efficient Synthesis of Halogenated Pyridin-2(1H)-ones
Zhang, Rui
Zhang, Dingyuan
Guo, Yongli
Zhou, Guangyuan
Jiang, Zijiang
Dong, Dewen
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23): : 9504 - 9507
[10] Synthesis of pyridin-2(1H)-ones by the intramolecular cyclization of amides of β-enamino ketones
D. S. Goncharov
A. S. Kostuchenko
A. S. Fisyuk
[J]. Chemistry of Heterocyclic Compounds, 2009, 45 : 793 - 795

← 1 2 3 4 5 →