Azabenzoquinolizines with Tranquillizing Activity

Abstract

Among the drugs with the ability to produce tranquillization, reserpine and its active analogues are characterized by a unique combination of pharmacological effects. Careful research into

Multicomponent Assembly Processes for the Synthesis of Diverse Yohimbine and Corynanthe Alkaloid Analogues

“…Compounds containing the pyrimidinedione ring exemplified in 39 are known to exhibit hypotensive, diuretic, and anti-anoxic effects. 16 In initial experiments toward accessing this heterocyclic systems, 9 was allowed to react with the silyl ketene acetal 36 17 in the presence of a sub-stoichiometric amount of TMSOTf. The putative intermediate amino ester 37 was then treated with phenylisocyanate to give the pyrimidinedione 39 , presumably by cyclization of 38 (Scheme 7).…”

Synthesis of pyrimido[6,1-a]isoquinolines via a one-pot, four-component reaction

“…[1][2][3][4] A broad range of biological activities has been reported for compounds containing the pyrimido-[6,1-a]isoquinoline ring system and a number of these compounds (pyrimidoisoquinoline derivatives 1) are patented as potential therapeutic agents (Scheme 1). 5,6 Amongst the reported ones are antihypertensive, bronchodilator, blood pressure lowering, anti inflammatory and anti-allergic activities. The antihypertensive agent Trequinsin 2 (Scheme 1), for instance, 7 is one of the most potent in vitro inhibitors of platelet phosphodiesterase and platelet aggregation known to date.…”

Multicomponent Assembly Strategies for the Synthesis of Diverse Tetrahydroisoquinoline Scaffolds

“…17 We were thus were intrigued by the possibility that we might exploit an MCAP/cyclization sequence to access this ring system by a route that would be more expedient than those previously reported. 17a,18 Indeed, sequential treatment of 1 with TMSOTf, the silyl ketene acetal 9 and phenyl isocyanate provided 15 in 63% yield (Scheme 3). Because an isocyanate is implemented as the electrophilic component, this series of reactions represents a significant expansion of our MCAP chemistry to give products containing urea functionality.…”