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. 2021 Jul 13;11(39):24466–24473. doi: 10.1039/d1ra04444c

Yields obtained in the synthesis of 1,5-benzodiazepines and 3.4-dihydroquinoxalines using deuterated acetonea.

Starting material X Product R1 R2 R3 R4 Acetone-d6 yield% (time)
6a O 10g H H Tetramethylbutyl CD3 57 (24 h)
6a O 10h H H Cyclohexyl CD3 61 (24 h)
6a O 11i H H t-Bu CD3 70 (24 h)
6c O 11j Cl Cl t-Bu CD3 72 (24 h)
6c O 11k Cl Cl Tetramethylbutyl CD3 80 (24 h)
a

Reaction conditions: isocyanide 2 (1 eq.), deuterated acetone 3c (2 eq.) and benzimidazole derivative 6 (1 eq.) were stirred at room temperature for 24 h.