Article: Oxidative addition of N-aminophthalimide to 3,4-dihydro-2H-thiopyrans, their S-oxides, and S,S-dioxides
Tetrahedron letters. 2022 Mar. 30, v. 94
2022
Abstract: ... obtained via addition of nitrene to the CC bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only ... en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped ...
Abstract | Selectivity of nitrene addition to the CCS fragment depends on the oxidative state of the sulfur atom as has been exemplified on various derivatives of 3,4-dihydro-2H-thiopyran under conditions of oxidative aminoaziridination. A unique structure with 2-thia-7-azabicyclo[4.1.0]heptane-2,2-dioxide core was obtained via addition of nitrene to the CC bond of thiopyran S,S-dioxide. For an unoxidized thiopyran, only en(phthaloyl)hydrazine resulted after cleavage of the initially formed aziridine. S-Oxide trapped the nitrene by the sulfur atom to form the sulfoximine leaving the double bond unaffected. |
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Keywords | ethyleneimine ; hydrazine ; sulfur |
Language | English |
Dates of publication | 2022-0330 |
Publishing place | Elsevier Ltd |
Document type | Article |
ZDB-ID | 204287-3 |
ISSN | 1873-3581 ; 0040-4039 |
ISSN (online) | 1873-3581 |
ISSN | 0040-4039 |
DOI | 10.1016/j.tetlet.2022.153715 |
Database | NAL-Catalogue (AGRICOLA) |
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