Katsuhiko Hino

Efficient stereospecific synthesis of (S,S)-3-methoxy-4-methylaminopyrrolidine

Abstract Efficient stereospecific synthesis of ( S , S )-3-methoxy-4-methylaminopyrrolidine, an important intermediate for a novel quinolone antitumor agent AG-7352 is presented. Starting from either d - or l -tartaric acid, a stereospecific synthesis of the chiral pyrrolidine was achieved via two S N 2 displacement reactions. From the results of this synthetic study, the absolute structure of AG-7352 was chemically determined.

Medicinal chemistry of 1-benzazepines

Publisher Summary This chapter discusses the medicinal chemistry of 1-Benzazepines. Many 1-benzazepines having various substituents possess interesting biological actions. Most of the actions of particular interest have been reported in the past decade. Numerous 1-benzazepine derivatives fused to an additional ring, especially with an aromatic ring, have been reported to exhibit a variety of biological activities, particularly on the central nervous system. The chapter presents the literature of the medicinal chemistry of those 1-benzazepine derivatives consisting of a fused two-ring system and the compounds without such framework to gain a better understanding of drug designs for the 1-benzazepine derivatives discussed. A variety of synthetic methods for 1-benzazepines has been reported and comprehensively reviewed. The main methods that appear to be of preparative value in the synthesis of 1-benzazepines are also summarized. The earliest synthetic method for 1-benzazepine derivatives was a ring closure of o -substituted anilines by C–N bond formation.