Efficient synthesis of 6-amino-substituted pyridin-2(1H)-ones using in situ generated propiolic acid chloride

被引：20

作者：

Schirok, H ^{[1
]}

Alonso-Alija, C ^{[1
]}

Michels, M ^{[1
]}

机构：

[1] Bayer HealthCare, Pharma Res, D-42096 Wuppertal, Germany

来源：

SYNTHESIS-STUTTGART | 2005年 / 18期

关键词：

pyridin-2(1H)-ones; cyclizations; thioacetals; N; S-acetals; ring closure;

D O I：

10.1055/s-2005-872217

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regioselective and highly efficient synthesis of 6-amino-substituted pyridin-2(1H)-ones is presented. In situ generated propiolic acid chloride was used for the cyclization of acyclic beta-keto N,S-acetals to afford the heterocyclic core. Substitution by amines led to a flexible access of the target compounds.

引用

页码：3085 / 3094

页数：10

共 50 条

[21] EFFICIENT SYNTHESIS OF CHIRAL 5-METHOXYCARBONYL-PYRIDIN-2(1H)-ONES AND 3-BROMO-5-METHOXYCARBONYL-PYRIDIN-2(1H)-ONES
Pilotzi, Hugo
Gnecco, Dino
Orea, Maria L.
Aparicio, David M.
Bernes, Sylvain
Juarez, Jorge R.
Teran, Joel L.
[J]. HETEROCYCLES, 2019, 98 (02) : 215 - 223
[22] Synthesis of diversely substituted pyridin-2(1H)-ones and in vivo evaluation of their anti-allodynic effect on cutaneous inflammatory mechanical allodynia
Frazier, Theo
Murail, Pauline
Boulange, Arthur
Chalane, Nazim
Giraud, Francis
Artola, Alain
Dallel, Radhouane
Anizon, Fabrice
Moreau, Pascale
[J]. RSC MEDICINAL CHEMISTRY, 2024, 15 (08): : 2900 - 2921
[23] Ring-Opening/Recyclization Reactions of (Dimethylamino)propenoyl-Substituted Cyclopropanes: Facile Synthesis of Halogenated Pyridin-2(1H)-ones
Zhang, Rui
Zhou, Yang
Liang, Yongjiu
Jiang, Zijiang
Dong, Dewen
[J]. SYNTHESIS-STUTTGART, 2009, (15): : 2497 - 2500
[24] New fragmentation processes of pyridin-2(1H)-ones upon electron impact ionization
Medina-Franco, JL
Juárez-Gordiano, C
Hernández-Campos, A
Duarte-Lisci, G
Guzmán, M
Castillo, R
[J]. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2005, 19 (16) : 2350 - 2354
[25] Synthesis of Pyridin-2(1H)-imines via the Transformation of Conjugated Ynones
Yang, Weiguang
Li, Guanrong
Huang, Zixin
Wang, Chen
Li, Hang
Zhou, Zitong
Mei, Shuangxi
Deng, Lu-Ming
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9139 - 9143
[26] 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
[27] Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes
Pan, Wei
Dong, Dewen
Wang, Kewei
Zhang, Jie
Wu, Rigenhada
Xiang, Dexuan
Liu, Qun
[J]. ORGANIC LETTERS, 2007, 9 (12) : 2421 - 2423
[28] 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
[29] Multicomponent cascade reaction of 3-formylchromones: Highly regioselective synthesis of functionalized pyridin-2(1H)-ones
Yun, Xinghan
Chen, Li
Lv, Ying
Lu, Zihan
Huang, Kun
Yan, Shengjiao
[J]. GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (03): : 231 - 239
[30] SYNTHESIS AND PROPERTIES OF 5-PYRIDYL-SUBSTITUTED 6-METHYL-4-(META-NITROPHENYL)-3-CYANOPYRIDIN-2(1H)-ONES, CORRESPONDING PYRIDIN-2(1H)-THIONES AND THEIR HYDROGENATED ANALOGS
KRAUZE, AA
ENSH, HI
DUBURS, GY
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (12): : 1674 - 1679

← 1 2 3 4 5 →