Aminomethylated Pyrroles: Casting a Spotlight

Roman, Gheorghe

doi:10.2174/157019306776819217

Cited by 10 publications

(1 citation statement)

References 83 publications

(176 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One of the possible ways to modify annelated pyrrolo[1,4]diazepines is the aminomethylation via Mannich reaction to give the corresponding Mannich bases. The reaction allows to prepare new aminomethylated derivatives which in turn, because of their high reactivity, can be applied as useful synthetic precursors : Mannich bases have been used as excellent H‐, C‐, N‐, O‐, S‐, and P‐alkylating agents because of their ability to replace the easily leaving dialkylamino group with other nucleophiles. Besides, diaklylamino group is a good precursor for the preparation of water‐soluble salts.…”

Section: Resultsmentioning

confidence: 99%

Annelated Pyrrolo[1,2-a][1,4]diazepines in Mannich Reaction

Строганова

Red'kin

Vasilin

et al. 2013

J. Heterocyclic Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Annelated Pyrrolo[1,2-a][1,4]diazepines in Mannich Reaction

Строганова

Red'kin

Vasilin

et al. 2013

J. Heterocyclic Chem.

View full text Add to dashboard Cite

Reusable Silica‐Supported Ammonium BINSate Catalysts for Enantio‐ and Diastereoselective Friedel–Crafts‐Type Double Aminoalkylation of N‐Alkylpyrroles with Aldimines

et al. 2020

View full text Add to dashboard Cite

Silica‐supported ammonium (R)‐BINSate catalysts for the enantio‐ and diastereoselective Friedel–Crafts‐type double aminoalkylation of N‐benzyl‐ or N‐methylpyrrole with aldimines were developed. The present heterogeneous catalysts showed high catalytic activity compared to our previous homogeneous (R)‐BINSA ammonium catalysts, which were effective for single aminoalkylation. Simple aldimines could be used, and the corresponding pyrrole‐derived chiral C2‐symmetric triamines were obtained in the dl‐form with good to extremely high enantioselectivities. The heterogeneous catalyst could be easily recovered and reused three times without any loss of catalytic activity or enantiocontrol. An XPS analysis supported precise preparation of the catalysts in situ and with good quality after recycling three times. From the perspective of modern green chemistry with fine asymmetric organocatalysis, the development of such chiral strong Brønsted acid catalysts might be useful for both laboratory and industrial applications.

show abstract