Iridium-Catalyzed C-H Amination/Cyclization for Medium to Large N-Heterocycle-Fused Dihydroquinazolinones

Tao Zhang, Xunqing Dong, Hitesh B. Jalani, Jiaqi Zou, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

A practical iridium-catalyzed cascade/stepwise synthesis of dihydroquinazolinones (DHQs) and bis-DHQs fused to medium to large N-heterocyclic rings is developed. The reaction undergoes benzamide-directed intermolecular C-H amination with an aldehyde-tethered alkyl azide, and then the newly installed amino group undergoes intramolecular cyclization with a remote aldehyde group present in azide and amidyl group of benzamide either intrinsically or catalyzed by phosphoric acid, facilitating the formation of bicyclic and/or tricyclic rings in a very efficient manner.

Original languageEnglish
Pages (from-to)3706-3710
Number of pages5
JournalOrganic Letters
Volume21
Issue number10
DOIs
StatePublished - May 17 2019

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