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

[31] Synthesis of 6,8-substituted imidazo[5,1-c]-[1,2,4]triazines and 1,4-dihydroimidazo[5,1-c]-[1,2,4]triazin-4-ones
Bezmaternykh, MA
Mokrushin, VS
Pospelova, TA
Eltsov, OS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (06): : 805 - 815
[32] Synthesis of pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones: Rearrangement of pyrrolo[1,2-d][1,3,4]oxadiazines and regioselective intramolecular cyclization of 1,2-biscarbamoyl-substituted 1H-pyrroles
Son, Kkonnip
Park, Seong Jun
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1780 - 1787
[33] Antitumour imidazotetrazines.: Part 36.: Conversion of 5-aminoimidazole-4-carboxamide to imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-ones and imidazo[1,5-a][1,3,5]triazin-4(3H)-ones related in structure to the antitumour agents temozolomide and mitozolomide
Wang, YF
Wheelhouse, RT
Zhao, LX
Langnel, DAF
Stevens, MFG
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (10): : 1669 - 1675
[34] Imidazo[1,2-a]pyrazin-8-ones, imidazo[1,2-d][1,2,4]triazin-8-ones and imidazo[2,1-f][1,2,4]triazin-8-ones as α2/α3 subtype selective GABAA agonists for the treatment of anxiety
Goodacre, SC
Hallett, DJ
Carling, RW
Castro, JL
Reynolds, DS
Pike, A
Wafford, KA
Newman, R
Atack, JR
Street, LJ
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) : 1582 - 1585
[35] Reactivity of 8-substituted 7-amino-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones
L. M. Mironovich
A. Yu. Podol’nikova
Russian Journal of Organic Chemistry, 2016, 52 : 453 - 455
[36] Reactivity of 8-substituted 7-amino-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones
Mironovich, L. M.
Podol'nikova, A. Yu.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (03) : 453 - 455
[37] Synthesis of 6,8-substituted derivatives of imidazo[5,1-c][1,2,4]triazines and 1,4-dihydroimidazo[5,1-c][1,2,4]triazin-4-ones
Bezmaternykh M.A.
Mokrushin V.S.
Pospelova T.A.
El'tsov O.S.
Chemistry of Heterocyclic Compounds, 1998, 34 (6) : 702 - 711
[38] Synthesis and reactivity of 7-amino-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-one
L. M. Mironovich
A. Yu. Podol’nikova
Russian Journal of General Chemistry, 2014, 84 : 2480 - 2482
[39] New Method for Synthesis of the Hetero-Cyclic System-1,2,3,4-Tetrahydro-Imidazo[5,1-f][1,2,4]Triazin-7-Amine
Vandyshev, D. Yu.
Shikhaliev, Kh. S.
Potapov, A. Yu.
Firgang, S. I.
Krysin, M. Yu.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (04) : 587 - 589
[40] Synthesis and Reactivity of 7-Amino-3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(6H)-one
Mironovich, L. M.
Podol'nikova, A. Yu.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (12) : 2480 - 2482

← 1 2 3 4 5 →