Synthesis of 1,2,5-oxadiazolyl-substituted imidazo[4,5-d]thiazolo[4,3-b]oxazoles

Synthesis of 1,2,5-oxadiazolyl-substituted imidazo[4,5-d]thiazolo[4,3-b]oxazoles Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2026, Volume: 75, Number: 4, Pages: 1193-1200 Pages count : 8 DOI: 10.1007/s11172-026-4971-9

Authors

Vinogradova E.E. ¹ , Larin A.A. ¹ , Gazieva G.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

1,3-Disubstituted 7-benzylidenehydrazono-4a-(1,2,5-oxadiazolyl)imidazo[4,5-d]-thiazolo[4,3-b]oxazoles were synthesized by the cascade reaction of 1,3-disubstituted N-(benzylideneamino)thioglycolurils with 3-(2-bromoacetyl)-4-methylfurazan and 4-(2-bromoacetyl)-3-phenylfuroxan. The reaction begins with the S-alkylation, followed by sequential nucleophilic addition, ring opening, and recyclization. The structures of the synthesized compounds were confirmed by IR, 1H, 13C, and 19F NMR spectroscopy and high-resolution mass spectrometry. For one of the reaction products, the structure and relative configurations of chiral centers were confirmed by X-ray diffraction analysis. The reaction was found to proceed with high diastereoselectivity to form rac-3aS,4aR,8aR-4a-(1,2,5-oxadiazolyl)imidazo[4,5-d]thiazolo[4,3-b]oxazoles in 35–50% yields.

Vinogradova E.E. , Larin A.A. , Gazieva G.A.
Synthesis of 1,2,5-oxadiazolyl-substituted imidazo[4,5-d]thiazolo[4,3-b]oxazoles
Russian Chemical Bulletin. 2026. V.75. N4. P.1193-1200. DOI: 10.1007/s11172-026-4971-9 OpenAlex

Виноградова Е.Е. , Ларин А.А. , Газиева Г.А.
Синтез 1,2,5-оксадиазолилзамещенных имидазо[4,5-d]тиазоло-[4,3-b]оксазолов
Известия Академии наук. Серия химическая. 2026. Т.75. №4. С.1193-1200.

Submitted:	Oct 6, 2025
Published online:	Jun 29, 2026

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