Direct Introduction of -OCD3 into the Hantzsch Pyrrole Synthesis via Multicomponent Cascade Cyclization: Synthesis of Fully Substituted Pyrrole Derivatives

Authors：Wang, Li-Sheng; Zhou, You; Lei, Shuang-Gui; Tang, Bo-Cheng; Yu, Zhi-Cheng; Tang, Yong-Xing; Wu, Yan-Dong; Wu, An-Xin^*

Source：Advanced Synthesis and Catalysis, 2023, 365(17): 2888-2893.

DOI：10.1002/adsc.202300629

• Hantzsch pyrrole synthesis
• deuterated alkoxy
• multicomponent cascade cyclization
• fully substituted pyrrole derivatives

A I-2-DMSO mediated approach to introduce -OCD3 into pyrroles in situ via multicomponent cascade cyclization reaction using methyl ketones, aniline, ethyl benzoylacetate and CD3OD as readily available substrates is reported. This process realizes introduction of -OCD3 into the Hantzsch pyrrole synthesis and synthesis of deuterated alkoxy-substituted pyrroles with formation of one C-C bond, one C-O bond and two C-N bonds in one pot. Notably, this conversion has good substrate compatibility (62 examples) and eliminates of the need for anhydrous and anaerobic operation.