Highly regioselective one-step synthesis of 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates

被引：3

作者：

Erdemir, Guler Yagiz ^{[1
]}

Altundas, Aliye ^{[1
]}

机构：

[1] Gazi Univ, Fac Sci, Dept Chem, TR-06560 Ankara, Turkiye

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2023年 / 59卷 / 4-5期

关键词：

aldehyde; 1,2,3-triazole; tri-tert-butoxyaluminum hydride; reduction; regioselective; AZIDE-ALKYNE CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITIONS; CLICK CHEMISTRY; DERIVATIVES; 1,2,3-TRIAZOLES; EFFICIENT; TRIAZOLE; ANALOGS;

D O I：

10.1007/s10593-023-03192-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology has been developed to afford 1,4,5-trisubstituted 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates in one step under mild conditions. This method includes the reduction of the ester functional group to an aldehyde using lithium tri-tert-butoxyaluminum hydride. Especially, this method offers a different perspective for fully substituted 1,2,3-triazoles with high regioselectivity and high yields. The structure of fully substituted triazoles was verified using FTIR, H-1, C-13 NMR spectroscopy, HRMS, advanced NMR techniques (COSY, C-APT, HSQC, and HMBC), and X-ray crystallography.

引用

收藏

页码：267 / 276

页数：10

相关论文

共 44 条

[1] DIPOLAR CYCLO-ADDITION REACTIONS OF ORGANIC AZIDES WITH SOME ACETYLENIC-COMPOUNDS [J].

ABUORABI, ST ;

ATFAH, MA ;

JIBRIL, I ;

MARII, FM ;

ALI, AAS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) :1461-1468

[2]

[Anonymous], 2014, APEX2 VERSION 2014 1

[3] An efficient and recyclable thiourea-supported copper(I) chloride catalyst for azide-alkyne cycloaddition reactions [J].

Barman, Milan Kr. ;

Sinha, Ashish Kumar ;

Nembenna, Sharanappa .

GREEN CHEMISTRY, 2016, 18 (08) :2534-2541

[4] Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation [J].

Baykal, Aslihan ;

Zhang, Dihan ;

Knelles, Jakob ;

Alt, Isabel T. ;

Plietker, Bernd .

CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (17) :3003-3010

[5] 1,2,3-triazolo[4,5-d]pyridazines -: Part VI.: New 1-substituted-4-amino derivatives and their affinity towards A1 and A2A adenosine receptors [J].

Biagi, G ;

Giorgi, I ;

Livi, O ;

Manera, C ;

Scartoni, V ;

Betti, L ;

Giannaccini, G ;

Lucacchini, A .

FARMACO, 1999, 54 (09) :615-623

[6] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].

Boren, Brant C. ;

Narayan, Sridhar ;

Rasmussen, Lars K. ;

Zhang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Jia, Guochen ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930

[7] 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].

Bozorov, Khurshed ;

Zhao, Jiangyu ;

Aisa, Haji A. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531

[8] STUDIES ON 1,2,3-TRIAZOLES .13. (PIPERAZINYLALKOXY)[1]BENZOPYRANO[2,3-D]-1,2,3-TRIAZOL-9(1H)-ONES WITH COMBINED H-1 ANTIHISTAMINE AND MAST-CELL STABILIZING PROPERTIES [J].

BUCKLE, DR ;

ROCKELL, CJM ;

SMITH, H ;

SPICER, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2262-2267

[9] Regioselective Reduction of 1H-1,2,3-Triazole Diesters [J].

Butler, Christopher R. ;

Bendesky, Justin ;

Schoffstall, Allen Milton .

MOLECULES, 2021, 26 (18)

[10]

Carey F. A., 2001, ADV ORGANIC CHEM B

← 1 2 3 4 5 →