88014-20-4Relevant academic research and scientific papers
HYDROBORATION OF 1-ALLYL-1,2,3,4-TETRAHYDROQUINOLINE
Kafka, Stanislav,Ferles, Miloslav,Richter, Miloslav
, p. 1194 - 1200 (2007/10/02)
Hydroboration of 1-allyl-1,2,3,4-tetrahydroquinoline (I) with triethylamine-borane in the molar ratio 1 : 1 afforded a product from which 6,7-benzo-5-aza-boraspirodecane (II) was isolated.Ethanolysis of II gave diethyl 3-(1,2,3,4-tetrahydro-1-quinolyl)propylborane (III).Acid hydrolysis led to a mixture of 3-(1,2,3,4-tetrahydro-1-quinolyl)-1-propanol (IV), 1,2,3,4-tetrahyroquinoline (V) and 1-propyl-1,2,3,4-tetrahydroquinoline (VI).Hydroboration of I with triethylamine-borane in the molar ratio 3 : 1, followed by oxidation, gave a mixture of IV, V, VI and 1-(1,2,3,4-tetrahydro-1-quinolyl)-2-propanol (VIII).Hydroboration of I with diborane in situ in diethylene glycol dimethyl ether at 20 deg C and subsequent acid hydrolysis and oxidation with alkaline hydrogen peroxide afforded a mixture of IV, V and VIII; when the hydroboration product was first heated to 150 deg C and then subjected to the above-mentioned processing, only compounds IV and V were formed.
