Synthese und Eigenschaften von 2,3‐Dihydro‐1H‐pyrrolizinen

Abstract

Die Darstellung von 2.3-Dihydro-lhl-pyrrolizinen aus 2-Alkyl-A 1-pyrrolinen in einer ,,Eintopfreaktion" wird beschrieben. Spektroskopische Daten und chemisches Verhalten dieser Verbindungen zeigen ihre Verwandtschaft zum Pyrrol-Grundkorper.

1-Pyrrolines (3,4-Dihydro-2H-pyrroles) as a Template for New Drugs

“…Easy access to the pyrrolizine nucleus is provided by the one-pot reaction of 1-pyrrolines with ω-halo ketones to yield a greater variety of alkyl and aryl substituted 2,3-dihydro-1H-pyrrolizines 7 (Scheme 3) which may be functionalized by reaction of different electrophilic compounds at the pyrrole moiety of the heterocyclic system [13] . A series of diarylpyrrolizine acetic acid derivatives 8 have been synthesized and widely investigated in the inhibition of cyclooxygenase-1, cyclooxygenase-2, lipoxygenase-5, and other enzymes involved in the arachidonic acid cascade.…”

Pyrrolo[2,1-a]isoquinolines (review)

“…Photographic filters were obtained as a result of the Chichibabin cyclization of the aromatic isoquinoline [149]. The reaction of 1-methyl-3,4-dihydroisoquinoline with bromoacetophenone [150,151] and also the cyclization of compound (LXXIX) with a-chloro ketones, e.g., with chloroagetoacetic ester, are known [152,153] In addition to the Chichibabin reaction, there are a whole group of methods for the condensation of 1methylisoquinoline with various electrophilic reagents, leading to the pyrrolo[2, l-a]isoquinoline system. The reaction of 1-methyl-3,4-dihydroisoquinoline with bromoacetophenone [150,151] and also the cyclization of compound (LXXIX) with a-chloro ketones, e.g., with chloroagetoacetic ester, are known [152,153] In addition to the Chichibabin reaction, there are a whole group of methods for the condensation of 1methylisoquinoline with various electrophilic reagents, leading to the pyrrolo[2, l-a]isoquinoline system.…”

(6,6-Dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)(thiophen-2-yl)methanone

“…For the synthesis of the title compound, see: Dannhardt & Obergrusberger (1979). For a similar structure, see: Liu et al (2007).…”

“…The title compound, (I) ( Fig. 1), 6-(2-thenoyl-)-7-phenyl-2,2-dimethyl-2,3-dihydro-1H-pyrrolizine was synthesized from 5-phenyl-3,3-dimethyl-3,4-dihydro-1H-pyrrolizine and 3-bromo-2-thenoylethanone according to a general literature of Dannhardt et al (1979).…”