Acid-Catalyzed Hydrolysis and Intramolecular Cyclization of N‑Cyano Sulfoximines for the Synthesis of Thiadiazine 1‑Oxides

Herein, we describe a novel approach for the practical synthesis of thiadiazine 1-oxides 10. The first example of an intramolecular cyclization with 2-N-cyano-sulfonimidoyl amides 9 to form the desired thiadiazine 1-oxides 10 was developed. One-pot acid-induced hydrolysis of the cyano group and the...

Full description

Saved in:
Bibliographic Details
Published inACS omega Vol. 7; no. 2; pp. 2160 - 2169
Main Authors Oh, In Seok, Seo, Ye Ji, Hyun, Ji Young, Lim, Hwan Jung, Lee, Duck-Hyung, Park, Seong Jun
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 18.01.2022
Online AccessGet full text

Cover

More Information
Summary:Herein, we describe a novel approach for the practical synthesis of thiadiazine 1-oxides 10. The first example of an intramolecular cyclization with 2-N-cyano-sulfonimidoyl amides 9 to form the desired thiadiazine 1-oxides 10 was developed. One-pot acid-induced hydrolysis of the cyano group and the intramolecular cyclocondensation protocol readily provided various heterocyclic frameworks in good to moderate yields. Notably, the crystal structures of N-urea sulfoximine 11 and thiadiazine 1-oxide 10i have been determined using X-ray crystallography.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c05570