The title compound, C(23)H(19)NO(5), was prepared by esterification of 2,2-bis-(hy-droxy-meth-yl)-2,3-dihydro-1H-pyrrolizin-1-one with benzoyl chloride in pyridine·The pyrrolizine ring system is approximately planar with a maximum deviation of 0.008 (2) Å from the least-squares plane; the two phenyl rings are oriented at dihedral angles of 64.26 (11) and 70.75 (10)° with respect to the pyrrolizine ring system. Weak inter-molecular C-H⋯O hydrogen bonding occurs in the crystal structure.
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http://dx.doi.org/10.1107/S1600536810051974 | DOI Listing |
Fitoterapia
December 2024
The Affiliated Dongguan Songshan Lake Central Hospital, Guangdong Medical University, College of Pharmacy, Guangdong Medical University, Dongguan 523808, China.
Leading by the antiviral activities against HSV-2 virus, bioactivity-guided the fraction of crude alkaloids from seeds of Peganum harmala led to the isolation of nine structurally novel indole alkaloids, pegaharolines A - I (1-9), and 11 known ones (10-20). Compound 3 was an unusual 6/5/5/5 spirotetracyclic indole-derived alkaloids featuring a classic bicyclic indole unit fused with an additional pyrrolizine ring via a spiral atom (C-3). Compound 4 was determined as a novel indole alkaloid, characterized with a rare hexacyclic 6/5/6/5-6/6 ring system, by a single-crystal X-ray diffraction.
View Article and Find Full Text PDFOrg Biomol Chem
September 2024
Department of Chemistry, University of Calcutta, 92 A. P. C. Road, Kolkata-700009, India.
Azomethine ylides are generated using either organocatalysts or metal catalysts a ballet of decarboxylative C-N coupling choreographed by prolines. These strategies enable diastereoselective [3 + 2] cycloaddition, C-C coupling, and ring annulation, providing sustainable routes. The synthesized pyrrolizines and other heterocycles have potential applications in the development of crucial biomolecules and pharmaceuticals.
View Article and Find Full Text PDFOrg Lett
November 2023
College of Chemistry and Materials Science, Chemical Biology Key Laboratory of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Hebei University, Baoding 071002, China, and.
NHC-catalyzed diastereoselective and enantioselective [12 + 2] higher-order cycloadditions of 5H-benzo[a]-pyrrolizine-3-carbaldehydes with cyclic sulfonic imines are described. Various optically pure polycyclic piperazin-2-ones were successfully constructed under mild reaction conditions with excellent diastereoselectivities and enantioselectivities. The generated chiral polycyclic piperazin-2-ones could be transformed to planar-chiral nine-membered cyclic amides via squaramide-catalyzed asymmetric ring-expansion reactions.
View Article and Find Full Text PDFBeilstein J Org Chem
October 2021
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa.
A wide range of -(ethoxycarbonylmethyl)enaminones, prepared by the Eschenmoser sulfide contraction between -(ethoxycarbonylmethyl)pyrrolidine-2-thione and various bromomethyl aryl and heteroaryl ketones, underwent cyclization in the presence of silica gel to give ethyl 6-(hetero)aryl-2,3-dihydro-1-pyrrolizine-5-carboxylates within minutes upon microwave heating in xylene at 150 °C. Instead of functioning as a nucleophile, the enaminone acted as an electrophile at its carbonyl group during the cyclization. Yields of the bicyclic products were generally above 75%.
View Article and Find Full Text PDFTop Curr Chem (Cham)
August 2021
Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Via Archirafi 32, 90123, Palermo, Italy.
The five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring-a phenomenon called "pseudorotation". In this review, we report bioactive molecules with target selectivity characterized by the pyrrolidine ring and its derivatives, including pyrrolizines, pyrrolidine-2-one, pyrrolidine-2,5-diones and prolinol described in the literature from 2015 to date.
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