Modular synthesis of triaroyl cyclopropanes via a formal cyclotrimerization of phenacyl bromides and their transformation into diazabicycles

TitleModular synthesis of triaroyl cyclopropanes via a formal cyclotrimerization of phenacyl bromides and their transformation into diazabicycles
Publication TypeJournal Article
Year of Publication2026
AuthorsJadhav, HMadhavrao, Penta, S, Pannuri, LLahari, Rangarao, C, Gonnade, RG, Manda, R
JournalOrganic Letters
Volume28
Issue20
Pagination6196-6201
Date PublishedMAY
Type of ArticleArticle
ISSN1523-7060
Abstract

Step-efficient cyclotrimerization reactions are entrancing approaches for saturated carbocycles. In this context, we demonstrate the alpha-bromocarbonyl (1+1+1) cyclotrimerization modularity to obtain stereoselective trisubstituted cyclopropanes under metal-free conditions. These cyclopropanes were condensed with hydrazine to afford diazabicyclic adducts and further expanded through a ring expansion reaction. In contrast to the classical alkylating reactivity, alpha-bromocarbonyl cyclotrimerization was also achieved by using various nucleophiles. A wide range of bromoacyl substrates established the broad scope of the transformation.

DOI10.1021/acs.orglett.6c01133
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.3

Divison category: 
Physical and Materials Chemistry
Database: 
Web of Science (WoS)

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