Synthesis of C6-Substituted Isoquinolino[1,2- b]quinazolines via Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides

Jin Zhang, Xiaogang Wang, Di Chen, Yifan Kang, Yangmin Ma, Michal Szostak

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

We report the synthesis of C6-substituted isoquinolino[1,2-b]quinazolinones via rhodium(III)-catalyzed C-H annulation with sulfoxonium ylides and evaluation of the cytotoxic activity of the scaffold. This C-H activation approach enables the most straightforward and convergent synthesis of C6-substituted isoquinolino[1,2-b]quinazolines reported to date. This operationally simple method is compatible with a wide variety of the sulfoxonium ylide and arene C-H activation coupling partners, permitting access to diverse isoquinolino[1,2-b]quinazolines. This method shows a high atom economy, generating H2O and dimethyl sulfoxide (DMSO) as by-products. This method is scalable and operates with exquisite N-lactam cyclization selectivity, thus enabling expedient access to new heterocyclic analogues featuring promising cytotoxic properties.

Original languageEnglish (US)
Pages (from-to)3192-3201
Number of pages10
JournalJournal of Organic Chemistry
Volume85
Issue number5
DOIs
StatePublished - Mar 6 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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