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

The Journal of organic chemistry 2020 Mar 06

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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.

Citation

Jin Zhang, Xiaogang Wang, Di Chen, Yifan Kang, Yangmin Ma, Michal Szostak. Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides. The Journal of organic chemistry. 2020 Mar 06;85(5):3192-3201