Journal of Organic Chemistry p. 3965 - 3970 (1981)
Update date:2022-08-10
Topics:
Minter, David E.
Stotter, Philip L.
Two efficient preparations of N-(carboalkoxy)-1,2-dihydroquinolines have been demonstrated.The first method involves direct acylation of the 1,2-hydroalumination adducts derived from quinolines and DIBAH.Overall yields range from 59percent to 82percent for reduction/acylation of simple quinolines including those with alkyl substituents at C-2.This method can be readily applied to large-scale reactions; however, it does not appear to be compatible with acid-sensitive functionalities.The second method is a complementary procedure involving reduction of quinoline N-boranes (generated by addition of BH3*THF to quinolines) with sodium dialkoxyaluminium dihydride at -78 deg C followed by in situ acylation of the intermediate aminoborohydride.Overall yields of products derived by this method are quite high (87-92percent) for a number of examples including very electron-rich quinolines and systems containing Lewis acid labile groups such as acetals.However, quinoline-N-boranes with C-2 alkyl substituents fail to undergo 1,2-reduction.Both methods generate N-(carboalkoxy)-1,2-dihydroquinolines which are uncontaminated by impurities derived from 1,4-dihydroquinoline and 1,2,3,4-tetrahydroquinoline byproducts.
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