Sinteza nove piridinijeve soli s triazolilidenskim fragmentom

diplomsko delo

Luka Jedlovčnik (Author), Janez Košmrlj (Mentor)

Abstract

Diplomsko delo opisuje sintezo nove, v literaturi še neopisane soli piridina s triazolilidenskim fragmentom vezanim na piridinski dušikov atom. Sintetizirana sol predstavlja potencialni bidentatni dikarbenski NHC ligand, uporaben za tvorbo NHC kompleksov s kovinami prehoda. Sintezo smo izvedli v šestih korakih, kjer smo najprej po literaturno znanih postopkih ločeno pripravili izhodni alkin, 1-etinil-4-fenilpiridin-1-ijev trifluorometansulfonat, in benzil azid. V nadaljevanju smo izvedli klik reakcijo med želenim alkinom in azidom, pri čemer smo dobili ustrezni triazol, 1-(1-benzil-1H-1,2,3-triazol-4-il)-4-fenilpiridin-1-ijev trifluorometansulfonat. Kot katalizator smo uporabili Cu(PPh3)3Br. V zadnjem koraku smo triazol metilirali na mestu N3 in tako prišli do končnega produkta, 1-(1-benzil-3-metil-1H-1,2,3-triazol-3-ijev-4-il)-4-fenilpiridin-1-ijevega trifluorometansulfonata. Končnega produkta nam žal ni uspelo očistiti, saj je razpadel na SiO2 koloni.

Keywords

1,2,3-triazol;triazolijeve soli;soli piridina;triazoliliden;ligand;klik reakcija;diplomska dela;

Data

Language:	Slovenian
Year of publishing:	2020
Typology:	2.11 - Undergraduate Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[L. Jedlovčnik]
UDC:	547.79:547.82(043.2)
COBISS:	30426883
Views:	444
Downloads:	111
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Synthesis of novel pyridinium salt containing triazolylidene fragment
Secondary abstract:	This thesis describes the synthesis of a novel pyridinium salt bearing triazolylidene fragment bounded to pyridine nitrogen atom, which has not yet been described in the literature. The synthesized salt represents a potential bidentate dicarbene NHC ligand, useful for the formation of transition metal NHC complexes. The synthesis was performed in six steps, where the starting alkyne, 1-ethynyl-4-phenylpyridin-1-trifluoromethanesulfonate, and benzyl azide, were independently prepared according to the literature reports. Following, a Cu(PPh3)3Br catalyzed click reaction between the desired alkyne and azide was performed to give the corresponding triazole, 1- (1-benzyl-1H-1,2,3-triazol-4-yl) -4-phenylpyridin-1-yl trifluoromethanesulfonate. In the last step, the triazole was methylated at the N3 position to give the final product, 1- (1-benzyl-3-methyl-1H-1,2,3-triazol-3-yl-4-yl) -4-phenylpyridin- 1-trifluoromethanesulfonate. Unfortunately, the final product was not purified, due to its decomposition on a SiO2 column.
Secondary keywords:	1,2,3-triazole;click reaction;triazolylidene;ligand;
Type (COBISS):	Bachelor thesis/paper
Study programme:	1000373
Embargo end date (OpenAIRE):	1970-01-01
Thesis comment:	Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages:	32 str.
ID:	12031350