beta-amino acids have been employed in the past as bifunctional building blocks in intramolecular Ugi multicomponent reactions to yield beta-lactam derivatives. By using 7-azabicyclo[2.2.1]heptane-2-carboxylic acid, a different outcome has been observed and rationalised. The final compounds are polyfunctionalised azabicyclic peptidomimetics, and further elaboration can be achieved exploiting an additional carboxylic group that is not involved in the multicomponent step.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b812304gDOI Listing

Publication Analysis

Top Keywords

intramolecular ugi
8
novel intramolecular
4
ugi reaction
4
reaction 7-azabicyclo[221]heptane
4
7-azabicyclo[221]heptane derivatives
4
derivatives post-condensation
4
post-condensation acylations
4
acylations entry
4
entry azanorbornyl
4
azanorbornyl peptidomimetics
4

Similar Publications

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light.

Beilstein J Org Chem

October 2024

Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, 1646 Genova, Italy.

Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of -aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine.

View Article and Find Full Text PDF

We report a two-step one-pot synthesis of the 2,6-diarylmorpholin-3-one core based on the Ugi reaction of 2-oxoaldehyde with 2-hydroxycarboxylic acid, a primary amine and -butyl isocyanide followed by a triflic acid-promoted intramolecular condensation accompanied by the loss of the isocyanide-originated amide moiety. The overall transformation proceeds with complete retention of stereoconfiguration at the 2-hydroxycarboxylic acid-derived chiral center, allowing the target morpholin-3-ones to be obtained in an enantiopure form. Subsequent double bond hydrogenation and amide reduction allow the degree of unsaturation to be reduced, providing a convenient entry to the -2,6-diphenylmorpholine motif.

View Article and Find Full Text PDF

Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition.

Chem Asian J

January 2025

Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, São Carlos - SP, 13565-905, Brazil.

The γ-lactam ring is a prominent feature in medicinal chemistry, and its synthesis has garnered significant interest due to its valuable properties. Among the γ-lactams, 2-oxopyrrolidine-3-carbonitrile derivatives stand out as versatile synthons that can be readily transformed into a variety of other functional groups. In this work, we successfully synthesized highly functionalized 3-cyano-2-pyrrolidinones with moderate to good overall yields using the Ugi reaction followed by intramolecular Michael addition.

View Article and Find Full Text PDF

Structurally diverse pyrroles, indoles and imidazoles bearing an -ω-azidoalkyl moiety and an aldehyde or ketone function were prepared and successfully introduced into imine generation the intramolecular Staudinger/aza-Wittig tandem reaction. Reduction of the generated imines led to medicinally relevant nitrogen-containing fused heterocycles such as tetrahydropyrrolo[1,2-]pyrazines and diazepines. Rare 8-membered hexahydropyrrolo[1,2-][1,4]diazocine and 9-membered dihydro-4,8-(metheno)pyrrolo[1,2-][1,4]diazacycloundecine were also synthesized.

View Article and Find Full Text PDF

A one-pot five component reaction for the synthesis of tetrazol-benzofuran hybrids and their inhibitory activity against .

Org Biomol Chem

September 2024

Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, Mexico.

A synthetic strategy for obtaining a new series of 1,5-disubstituted tetrazole-benzofuran hybrid systems a one-pot five-component reaction is described. This process involves a Ugi-azide multicomponent reaction coupled to an intramolecular cyclization catalyzed by Pd/Cu, resulting in low to moderate yields from 21 to 67%. This protocol allowed the synthesis of highly substituted benzofurans at the 2-position through an operationally simple process under mild reaction conditions and with high bond forming efficiency due to the formation of six new bonds (two C-C, two C-N, one N-N, and one C-O).

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!