Tandem Ring-Opening/Double Ring-Closing Synthesis of 1,2,4-Triazolo[1,5-a]pyridines from Chromone-Containing Acrylonitriles

被引：2

作者：

Chernov, Nikita M. ^{[1
]}

Kustin, Roman P. ^{[1
]}

Pypa, Yulia V. ^{[1
]}

Anisimov, Sergej O. ^{[1
]}

Spiridonova, Dar'ya V. ^{[2
]}

Shutov, Roman V. ^{[1
]}

Yakovlev, Igor P. ^{[1
]}

机构：

[1] St Petersburg State Chem & Pharmaceut Univ, Dept Organ Chem, Prof Popov St 14, St Petersburg 197376, Russia

[2] St Petersburg State Univ, Res Pk, Univ Nab 7-9, St Petersburg 199034, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 02期

关键词：

amphiphiles; cyclization; chromones; heterocycles; hydrazides; nucleophilic addition; DOMINO PROCESS; 3-FORMYLCHROMONES; CONSTRUCTION; DERIVATIVES; CYCLIZATION; DIVERSITY; SCAFFOLDS; ROUTE;

D O I：

10.1002/adsc.202300934

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We studied a reaction of chromone-containing acrylonitriles and cyanoacrylates with acid hydrazides. This reaction turned out to be a method for the synthesis of salicyloyl-substituted 1,2,4-triazolo[1,5-a]pyridines. The synthesis developed is a tandem ring-opening/double ring-closing process. This synthetic approach is characterized by low toxic solvents (ethanol, butanol) and mediator (Et3N), 37-84% yields, non-chromatographic isolation of products, and substrate tolerance (59 examples).

引用

页码：277 / 284

页数：8

共 58 条

[1] Unorthodox synthesis, biological activity and DFT studies of novel and multifunctionalized naphthoxocine derivatives
Abozeid, Mohamed Ahmed
El-Sawi, Aya Atef
Elmorsy, Mohamed Ramadan
Abdelmoteleb, Mohamed
Abdel-Rahman, Abdel-Rahman Hassan
El-Desoky, El-Sayed Ibrahim
[J]. RSC ADVANCES, 2019, 9 (48) : 27996 - 28005
[2] Revisited synthesis of fused diazepines from 3-(3-aryl-3-oxopropenyl)chromen-4-ones and binucleophilic amino enones in a three-step domino process
Alizadeh, Abdolali
Bagherinejad, Akram
[J]. MENDELEEV COMMUNICATIONS, 2023, 33 (03) : 401 - 403
[3] Recyclization of 3-formylchromone with phenacyl thiocyanate: fast and efficient access to thiophenes and 2-aminothiophenes bearing o-acylphenol moiety
Alizadeh, Abdolali
Rezaiyehraad, Reza
[J]. JOURNAL OF SULFUR CHEMISTRY, 2022, 43 (03) : 264 - 274
[4] [Anonymous], 2021, CrysAlisPro1.171.41.103a
[5] Badran A.-S., 2020, J HETEROCYCLIC CHEM, V57, P2297
[6] Synthesis, spectral characterization, DFT and in silico ADME studies of the novel pyrido[1,2-a]benzimidazoles and pyrazolo[3,4-b]pyridines
Badran, Al-Shimaa
Ibrahim, Magdy A.
[J]. JOURNAL OF MOLECULAR STRUCTURE, 2023, 1274
[7] A Convenient Method for the Synthesis of Imidazo[1,2-a]pyridines with a New Approach
Balalaie, Saeed
Derakhshan-Panah, Fatemeh
Zolfigol, Mohammad Ali
Rominger, Frank
[J]. SYNLETT, 2018, 29 (01) : 89 - 93
[8] A catalyst- and solvent-free thermal multicomponent approach for the construction of diverse and polysubstituted 2-aminopyridines and their antibacterial activity
Baral, Ek Raj
Sharma, Kavita
Akhtar, Muhammad Saeed
Lee, Yong Rok
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (43) : 10285 - 10297
[9] Regioselective Synthesis of Novel [1,2,4]Triazolo[1,5-a]pyridine Derivatives
Ben Hassen, Manel
Masmoudi, Fatma
Zribi, Lazhar
Trigui, Mohamed
Ismaili, Lhassane
Marco-Contelles, Jose
Chabchoub, Fakher
[J]. CHEMISTRYSELECT, 2021, 6 (05): : 945 - 950
[10] The Modern Face of Synthetic Heterocyclic Chemistry
Cabrele, Chiara
Reiser, Oliver
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (21) : 10109 - 10125

← 1 2 3 4 5 6 →