56503-48-1Relevant articles and documents
Efficient Conversions of Quinolines to N-(Carboalkoxy)-1,2-dihydroquinolines
Minter, David E.,Stotter, Philip L.
, p. 3965 - 3970 (1981)
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.
Synthesis of novel heterocycles related to the dynemicin A ring skeleton
Nicolaou,Gross,Gross, Jonathan L.,Kerr,Kerr, Michael A.
, p. 735 - 746 (2007/10/03)
Studies directed towards the construction of the CDE ring framework of dynemycin A (1) are reported. A series of quinoline based dienophiles containing an activating group (e.g. 5), reacted with acyclic dienes (e.g. 4) in a Diels-Alder fashion under incre
