Conclusions
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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.
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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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Literature cited
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1413–1415, June, 1988.
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Shmyreva, Z.V., Shikhaliev, K.S., Shapiro, A.B. et al. Reaction of dichlorocarbene with 2,2,4-trimethyl-1,2-dihydroquinoline and its derivatives. Russ Chem Bull 37, 1248–1250 (1988). https://doi.org/10.1007/BF00961945
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DOI: https://doi.org/10.1007/BF00961945