Reaction of dichlorocarbene with 2,2,4-trimethyl-1,2-dihydroquinoline and its derivatives
1988
1.
The reaction of dichlorocarbene with 6-R-2,2,4-trimethyl-1,2-dihydroquinolines gives formylation at the N-H bond followed by [1+2] cycloaddition at the double bond with formation of the corresponding 7-R-1-formyl-2,2,5-trimethyl-4,4-dichlorocyclopropane[c]-quinolines.
2.
The yields of the [1+2] cycloaddition products decreases with increasing nucleophilicity of the nitrogen atom in the dihydroquinoline ring.
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