6590-70-1Relevant academic research and scientific papers
Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline
Miyata, Okiko,Shirai, Atsushi,Yoshino, Shintaro,Nakabayashi, Toshiki,Takeda, Yoshifumi,Kiguchi, Toshiko,Fukumoto, Daisuke,Ueda, Masafumi,Naito, Takeaki
, p. 10092 - 10117 (2008/02/13)
Radical addition-cyclization-elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu3SnNMe2, Bu3SnD, and/or D2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.
NEW APPROACH TO THE SYNTHESIS OF DERIVATIVES OF AZABICYCLONONANE WITH VARIOUS HETEROATOMS IN THE MACROCYCLE
Ukhin, L. Yu.,Komissarov, V. N.,Korobov, M. S.,Nivorozhkin, L. E.
, p. 331 - 335 (2007/10/02)
The reaction of aromatic aldehydes containing functional groups having mobile hydrogen atoms at the ortho position with primary amines leads both to Schiff bases and to the products from intramolecular condensation (derivatives of azabicyclononane)
