Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes
- 1N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russia
- 2A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, Moscow 119991, Russia
Abstract
A convenient method is described for the synthesis of novel 2-arylazo-1,3,4-thiadiazines fused with pyridine, pyrimidine or pyrazole ring. The synthetic strategy relies on a one-pot tandem cascade that proceeds through three consecutive steps without the isolation of intermediates: (1) nucleophilic aromatic substitution (SNAr) of the chlorine atom by the dithizone nucleophile, (2) intramolecular S-N-type Smiles rearrangement involving migration of the hetaryl fragment from nitrogen to sulfur, and (3) intramolecular nucleophilic substitution of the activated nitro group, which closes the fused thiadiazine ring. The use of ortho-chloronitro hetarenes is essential, as the nitro group serves both as an activating substituent for the initial SNAr step and as a leaving group in the final cyclization step. UV-Vis absorption spectra of the synthesized compounds were recorded.
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BibTeX
@article{nikolskiy2026simple,
title = {{Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes}},
author = {Vladislav V. Nikol’skiy and Alexey M. Starosotnikov and Alexey K. Fedorenko and Ivan V. Fedyanin and Artem N. Fakhrutdinov and Maxim A. Bastrakov},
journal = {International journal of molecular sciences},
year = {2026},
month = oct,
doi = {10.3390/ijms27198886},
url = {https://europepmc.org/article/PMC/PMC13665132},
note = {CC BY},
}
RIS
TY - JOUR
TI - Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes
AU - Vladislav V. Nikol’skiy
AU - Alexey M. Starosotnikov
AU - Alexey K. Fedorenko
AU - Ivan V. Fedyanin
AU - Artem N. Fakhrutdinov
AU - Maxim A. Bastrakov
PY - 2026
DA - 2026/10/01
JO - International journal of molecular sciences
DO - 10.3390/ijms27198886
UR - https://europepmc.org/article/PMC/PMC13665132
AB - A convenient method is described for the synthesis of novel 2-arylazo-1,3,4-thiadiazines fused with pyridine, pyrimidine or pyrazole ring. The synthetic strategy relies on a one-pot tandem cascade that proceeds through three consecutive steps without the isolation of intermediates: (1) nucleophilic aromatic substitution (SNAr) of the chlorine atom by the dithizone nucleophile, (2) intramolecular S-N-type Smiles rearrangement involving migration of the hetaryl fragment from nitrogen to sulfur, and (3) intramolecular nucleophilic substitution of the activated nitro group, which closes the fused thiadiazine ring. The use of ortho-chloronitro hetarenes is essential, as the nitro group serves both as an activating substituent for the initial SNAr step and as a leaving group in the final cyclization step. UV-Vis absorption spectra of the synthesized compounds were recorded.
SN - 1422-0067
ER -