Concise Synthesis of Versatile Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones

被引：6

作者：

Tran, Tuan P. ^{[1
]}

Fisher, Ethan L. ^{[1
]}

Wright, Ann S. ^{[1
]}

Yang, Jiao ^{[2
]}

机构：

[1] Pfizer Worldwide Res & Dev, Eastern Point Rd, Groton, CT 06340 USA

[2] WuXi AppTec, 288 Fute Zhong Rd, Shanghai 200131, Peoples R China

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2018年 / 22卷 / 02期

关键词：

N-AMINATION; PHOSPHODIESTERASE; HETEROCYCLES;

D O I：

10.1021/acs.oprd.7b00333

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of a series of imidazo[S,1-f][1,2,4]triazin-4(3H)-ones was developed from starting imidazoles in three linear steps. The synthetic sequence began with an electrophilic amination and thus a rigorous campaign to identify safe reagent and reaction conditions was performed to ensure safety for preparation of these versatile intermediates on large scales. Functionalizations at the key positions on these substrates were exemplified to demonstrate ability to perform late-stage diversification for efficient SAR discovery.

引用

页码：166 / 172

页数：7

共 50 条

[41] A Simple and Efficient Approach for the Synthesis of Aryl-3-(trifluoromethyl)-1 H -1,2,4-triazol-5(4 H )-one Derivatives
Kazemi, Elham
Zeinali, Najmeh
Darehkordi, Ali
SYNTHESIS-STUTTGART, 2024, 56 (12): : 1941 - 1957
[42] Synthesis and tautomeric structure of 6-arylhydrazono 1H-pyrazolo[3′,4′:4,5]-pyrimidol[1,6-b][1,2,4]triazepines
Shawali, Ahmad S.
Farghaly, Thoraya A.
TETRAHEDRON, 2009, 65 (03) : 644 - 647
[43] Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles
Mei, Haibo
Xiong, Yiwen
Xie, Chen
Soloshonok, Vadim A.
Han, Jianlin
Pan, Yi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (13) : 2108 - 2113
[44] Synthesis of bis[1,2,4]triazolo[4,3-b:1′,5′-d][1,2,4]triazine, a novel polynitrogenated heterocyclic system
Nasser Montazeri
Majid M. Heravi
Farzaneh Tajfirooz
Niousha Nazari
Monatshefte für Chemie - Chemical Monthly, 2017, 148 : 691 - 694
[45] Synthesis of bis[1,2,4]triazolo[4,3-b:1',5'-d][1,2,4]triazine, a novel polynitrogenated heterocyclic system
Montazeri, Nasser
Heravi, Majid M.
Tajfirooz, Farzaneh
Nazari, Niousha
MONATSHEFTE FUR CHEMIE, 2017, 148 (04): : 691 - 694
[46] Synthesis of chromeno[3,4-b]pyrrol-4(3H)-ones by cyclocondensation of 1,3-dicarbonyl compounds with 4-chloro-3-nitrocoumarin
Zeeshan, Muhammad
Iaroshenko, Viktor O.
Dudkin, Sergii
Volochnyuk, Dmitriy M.
Langer, Peter
TETRAHEDRON LETTERS, 2010, 51 (30) : 3897 - 3898
[47] Regiocontrolled Synthesis of 6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazines
Lindsay-Scott, Peter J.
Rivlin-Derrick, Eloise
SYNTHESIS-STUTTGART, 2020, 52 (01): : 105 - 118
[48] Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1-c][1,2,4]triazolo[3,4-f][1,2,4]triazines
El Azab, Islam H.
Elkanzi, Nadia A. A.
MOLECULES, 2020, 25 (06):
[49] Microwave-Assisted Three-Component Reaction for the Synthesis of Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones
Mert-Balci, Fadime
Conrad, Juergen
Meindl, Kathrin
Schulz, Thomas
Stalke, Dietmar
Beifuss, Uwe
SYNTHESIS-STUTTGART, 2008, (22): : 3649 - 3656
[50] Regioselective Synthesis of Imidazo[4,5-e][1,3]Thiazino[3,2-b][1,2,4]Triazines as New Heterocyclic System Derivatives
Izmest'ev, Alexei N.
Baranov, Vladimir V.
Kolotyrkina, Natalya G.
Kravchenko, Angelina N.
Gazieva, Galina A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, : 58 - 64

← 1 2 3 4 5 →