Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes

Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes Full article

Journal

International Journal of Molecular Sciences
ISSN: 1661-6596 , E-ISSN: 1422-0067

Output data

Year: 2026, Volume: 27, Number: 19, Article number : 8886, Pages count : 13 DOI: 10.3390/ijms27198886

Tags

nitro group; nucleophilic aromatic substitution; Smiles rearrangement; pyr-ido[2,3-e][1,3,4]thiadiazines; pyrimido[4,5-e][1,3,4]thiadiazines; 1,5-dihydropyrazolo[4,3-e][1,3,4]thiadiazines; dithizones; UV-Vis spectroscopy

Authors

Nikol’skiy Vladislav V. ¹ , Starosotnikov Alexey M. ¹ , Fedorenko Alexey K. ¹ , Fedyanin Ivan V. ² , Fakhrutdinov Artem N. ¹ , Bastrakov Maxim A. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russia
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, Moscow 119991, Russia

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 mi-gration of the hetaryl fragment from nitrogen to sulfur, and (3) intramolecular nucleo-philic 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 cycliza-tion step. UV-Vis absorption spectra of the synthesized compounds were recorded.

Nikol’skiy V.V. , Starosotnikov A.M. , Fedorenko A.K. , Fedyanin I.V. , Fakhrutdinov A.N. , Bastrakov M.A.
Simple Synthesis of Fused 1,3,4-Thiadiazines Through Successive SNAr Processes
International Journal of Molecular Sciences. 2026. V.27. N19. 8886 :1-13. DOI: 10.3390/ijms27198886 OpenAlex

Submitted:	Aug 31, 2026
Accepted:	Oct 1, 2026
Published online:	Oct 6, 2026

≡ OpenAlex:

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