Issue 33, 2022

Synthesis of spiropyrans via the Rh(iii)-catalyzed annulation of 3-aryl-2H-benzo[b][1,4]oxazines with diazo ketoesters

Abstract

Rh(III)-Catalyzed 1 : 2 coupling of 3-aryl-2H-benzo[b][1,4]oxazines with α-diazo-β-ketoesters has been realized for the mild synthesis of spiropyrans. The reaction proceeded via twofold C–H activation followed by unusual [3+3] and [4+2] annulation with decent functional group tolerance. Moreover, a pyranoid-skeleton intermediate was isolated as a key intermediate as a result of monoalkylation and enol oxygen annulation, which offers direct mechanistic insight.

Graphical abstract: Synthesis of spiropyrans via the Rh(iii)-catalyzed annulation of 3-aryl-2H-benzo[b][1,4]oxazines with diazo ketoesters

Supplementary files

Article information

Article type
Communication
Submitted
14 fev 2022
Accepted
18 mar 2022
First published
18 mar 2022

Chem. Commun., 2022,58, 5144-5147

Synthesis of spiropyrans via the Rh(III)-catalyzed annulation of 3-aryl-2H-benzo[b][1,4]oxazines with diazo ketoesters

J. J. Zhang, M. Zhang, M. Lu, Y. He, S. Li, L. Fan, X. Zhang, J. Wu and X. Yang, Chem. Commun., 2022, 58, 5144 DOI: 10.1039/D2CC00916A

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