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  2. All Volumes and Issues
  3. Volume 17, Number 2, 2023
  4. The (1H-Tetrazol-1-yl)arenediazonium Salts as Convenient Reagents for Quinones Arylation: Synthesis of 1,3-Benzoxathiol-2-ones and Naphtho[2,1-d][1,3]oxathiol-2-ones Bearing (1H-Tetrazol-1-yl)phenyl Motif

The (1H-Tetrazol-1-yl)arenediazonium Salts as Convenient Reagents for Quinones Arylation: Synthesis of 1,3-Benzoxathiol-2-ones and Naphtho[2,1-d][1,3]oxathiol-2-ones Bearing (1H-Tetrazol-1-yl)phenyl Motif

JCCT.
2023;
Volume 17, Number 2
: pp. 304 - 314
https://doi.org/10.23939/chcht17.02.304
Authors:
  1. Nazariy Pokhodylo
  2. Roman Martyak
  3. Mykola Тupychak
  4. Khrystyna Pitkovych
  5. Vasyl Matiychuk
  6. Mykola Obushak
1
Ivan Franko National University of Lviv
2
Ivan Franko National University of Lviv
3
Ivan Franko National University of Lviv
4
Ivan Franko National University of Lviv
5
Ivan Franko National University of Lviv
6
Ivan Franko National University of Lviv

A convenient two-step method for the synthesis of novel 1,3-benzoxathiol-2-ones and naphtho[2,1-d][1,3]oxathiol-2-ones bearing (1H-tetrazol-1-yl)phenyl motif was developed. As a key step of the synthesis, an arylation of quinones (1,4-benzoquinone, 1,4-naphtho-quinones) with the (1H-tetrazol-1-yl)arenediazonium salts was studied and efficient protocols were elaborated to obtain a variety of substituted ((1H-tetrazol-1-yl)phenyl) benzo/naphtho-1,4-quinones in good to excellent yields. An alternative synthesis of ((1H-tetrazol-1-yl)phenyl) naphtho-1,4-quinones via Diels-Alder reaction of tetrazolylphenyl-1,4-benzoquinones was demonstrated. The prepared benzo/naphtho-1,4-quinones readily react with thiourea at room temperature in the presence of a strong mineral acid to form intermediate isothiuronium salts, which cyclize with high yields to condense 1,3-oxathiol-2-ones under heating.

tetrazole
quinone
oxathiolone
Meerwein arylation
cyclization
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