RADICAL CYCLIZATION AND 1,5-HYDROGEN TRANSFER IN SELECTED AROMATIC DIAZONIUM SALTS

Risultato della ricerca: Article

2 Citazioni (Scopus)

Abstract

2-(Methyl(3-methyl-1-phenyl-1H-pyrazol-5-yl)carbamoyl)thiophene-3-diazonium hydrogen sulfate 20, 2-(methyl(3-methyl-isoxazol-5yl)carbamoyl)-benzenediazonium hydrogen sulfate 21 and 2-(methyl(phenyl)carbamoyl)-benzenediazonium hydrogen sulphate 22 were synthesized and reacted with a CuSO4/NaCl/ascorbic acid combination to give complex mixtures. The structures of the reaction products were elucidated, depending upon the pathways followed. Compound 20 almost exclusively afforded an Ar-5 cyclization product and trace amounts of the product derived from a competing Ar-6 Pschorr closure. In the case of compound 21, the Ar-6 cyclization was not observed, while the Ar-5 cyclization and 1,5-hydrogen radical transfer processes equally occurred. Finally, the Ar-6 cyclization was observed as the main process for compound 22, accompanied by the Ar-5 cyclization and, in a much lesser extent, by an 1,5-hydrogen radical transfer process.
Lingua originaleEnglish
pagine (da-a)83-101
Numero di pagine19
RivistaHeterocycles
Volume89
Stato di pubblicazionePublished - 2014

Fingerprint

Cyclization
Hydrogen
Salts
Sulfates
Thiophenes
Complex Mixtures
Reaction products
Ascorbic Acid
benzenediazonium

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cita questo

RADICAL CYCLIZATION AND 1,5-HYDROGEN TRANSFER IN SELECTED AROMATIC DIAZONIUM SALTS. /.

In: Heterocycles, Vol. 89, 2014, pag. 83-101.

Risultato della ricerca: Article

@article{a6a92d005a9447349b60e633f384fb0e,
title = "RADICAL CYCLIZATION AND 1,5-HYDROGEN TRANSFER IN SELECTED AROMATIC DIAZONIUM SALTS",
abstract = "2-(Methyl(3-methyl-1-phenyl-1H-pyrazol-5-yl)carbamoyl)thiophene-3-diazonium hydrogen sulfate 20, 2-(methyl(3-methyl-isoxazol-5yl)carbamoyl)-benzenediazonium hydrogen sulfate 21 and 2-(methyl(phenyl)carbamoyl)-benzenediazonium hydrogen sulphate 22 were synthesized and reacted with a CuSO4/NaCl/ascorbic acid combination to give complex mixtures. The structures of the reaction products were elucidated, depending upon the pathways followed. Compound 20 almost exclusively afforded an Ar-5 cyclization product and trace amounts of the product derived from a competing Ar-6 Pschorr closure. In the case of compound 21, the Ar-6 cyclization was not observed, while the Ar-5 cyclization and 1,5-hydrogen radical transfer processes equally occurred. Finally, the Ar-6 cyclization was observed as the main process for compound 22, accompanied by the Ar-5 cyclization and, in a much lesser extent, by an 1,5-hydrogen radical transfer process.",
author = "Benedetta Maggio and Demetrio Raffa and Gianfranco Fontana and Francesco Ferrante",
year = "2014",
language = "English",
volume = "89",
pages = "83--101",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",

}

TY - JOUR

T1 - RADICAL CYCLIZATION AND 1,5-HYDROGEN TRANSFER IN SELECTED AROMATIC DIAZONIUM SALTS

AU - Maggio, Benedetta

AU - Raffa, Demetrio

AU - Fontana, Gianfranco

AU - Ferrante, Francesco

PY - 2014

Y1 - 2014

N2 - 2-(Methyl(3-methyl-1-phenyl-1H-pyrazol-5-yl)carbamoyl)thiophene-3-diazonium hydrogen sulfate 20, 2-(methyl(3-methyl-isoxazol-5yl)carbamoyl)-benzenediazonium hydrogen sulfate 21 and 2-(methyl(phenyl)carbamoyl)-benzenediazonium hydrogen sulphate 22 were synthesized and reacted with a CuSO4/NaCl/ascorbic acid combination to give complex mixtures. The structures of the reaction products were elucidated, depending upon the pathways followed. Compound 20 almost exclusively afforded an Ar-5 cyclization product and trace amounts of the product derived from a competing Ar-6 Pschorr closure. In the case of compound 21, the Ar-6 cyclization was not observed, while the Ar-5 cyclization and 1,5-hydrogen radical transfer processes equally occurred. Finally, the Ar-6 cyclization was observed as the main process for compound 22, accompanied by the Ar-5 cyclization and, in a much lesser extent, by an 1,5-hydrogen radical transfer process.

AB - 2-(Methyl(3-methyl-1-phenyl-1H-pyrazol-5-yl)carbamoyl)thiophene-3-diazonium hydrogen sulfate 20, 2-(methyl(3-methyl-isoxazol-5yl)carbamoyl)-benzenediazonium hydrogen sulfate 21 and 2-(methyl(phenyl)carbamoyl)-benzenediazonium hydrogen sulphate 22 were synthesized and reacted with a CuSO4/NaCl/ascorbic acid combination to give complex mixtures. The structures of the reaction products were elucidated, depending upon the pathways followed. Compound 20 almost exclusively afforded an Ar-5 cyclization product and trace amounts of the product derived from a competing Ar-6 Pschorr closure. In the case of compound 21, the Ar-6 cyclization was not observed, while the Ar-5 cyclization and 1,5-hydrogen radical transfer processes equally occurred. Finally, the Ar-6 cyclization was observed as the main process for compound 22, accompanied by the Ar-5 cyclization and, in a much lesser extent, by an 1,5-hydrogen radical transfer process.

UR - http://hdl.handle.net/10447/85404

M3 - Article

VL - 89

SP - 83

EP - 101

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

ER -