Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts

A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C–N, C–C bond and an endocyclic double bond are f...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 17; pp. 11735 - 11742
Main Authors Sinka, Victoria, Fernández, Israel, Padrón, Juan I.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
POTENT
PYRROLIDINES
HETEROCYCLES
RING-EXPANSION
BIOLOGICAL-ACTIVITIES
CASCADE
STEREOSELECTIVE-SYNTHESIS
AZIRIDINES
METATHESIS
Online AccessGet full text

Cover

More Information
Summary:A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C–N, C–C bond and an endocyclic double bond are formed. Under mild reaction conditions and using iron­(III) salts as sustainable catalysts, tetrahydroazepines with different degrees of substitution are obtained directly and efficiently. DFT calculations supported the proposed mechanism.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01396