Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides

Trimurtulu Kotipalli, Veerababurao Kavala, Ashok Konala, Donala Janreddy, Chu Wei Kuo, Ching-Fa Yao

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).

Original languageEnglish
Pages (from-to)2652-2660
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number16
DOIs
Publication statusPublished - 2016 Jan 1

Fingerprint

Derivatives
Pyridine
Salts
Metals
1,2,4-triazole
1,3,4-oxadiazole
triflic anhydride
2-fluoropyridine
phenylhydrazine
pyridine

Keywords

  • 1,2,4-triazoles
  • 1,3,4-oxadiazoles/1,3,4-oxadiazolines
  • hydrazides
  • pyridine activation
  • switching

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides. / Kotipalli, Trimurtulu; Kavala, Veerababurao; Konala, Ashok; Janreddy, Donala; Kuo, Chu Wei; Yao, Ching-Fa.

In: Advanced Synthesis and Catalysis, Vol. 358, No. 16, 01.01.2016, p. 2652-2660.

Research output: Contribution to journalArticle

Kotipalli, Trimurtulu ; Kavala, Veerababurao ; Konala, Ashok ; Janreddy, Donala ; Kuo, Chu Wei ; Yao, Ching-Fa. / Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides. In: Advanced Synthesis and Catalysis. 2016 ; Vol. 358, No. 16. pp. 2652-2660.
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abstract = "A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).",
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AU - Kotipalli, Trimurtulu

AU - Kavala, Veerababurao

AU - Konala, Ashok

AU - Janreddy, Donala

AU - Kuo, Chu Wei

AU - Yao, Ching-Fa

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N2 - A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).

AB - A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).

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KW - switching

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