An efficient synthesis of 2-aminopyrroles from enaminone–amidine adduct and phenacyl/benzyl/heteroalkyl-halides

An efficient synthesis of 2-aminopyrroles from enaminone–amidine adduct and phenacyl/benzyl/heteroalkyl-halides

Herein, we report an efficient and facile synthesis of substituted 2-aminopyrroles from the reaction of enaminone–amidine adduct and various phenacyl, benzyl, or heteroalkyl halides in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in good to excellent yields. The reaction proceeds through...

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Veröffentlicht in:Tetrahedron letters 2011-11, Vol.52 (48), p.6331-6335
Hauptverfasser: Jalani, Hitesh B., Pandya, Amit N., Baraiya, Arshi B., Kaila, Jitendra C., Pandya, Dhaivat H., Sharma, Jayesh A., Sudarsanam, V., Vasu, Kamala K.
Format: Artikel
Sprache:eng
Schlagworte:
2-Aminopyrroles
5-Exo trig
Adducts
Chemistry
Cyanamide
Enaminone
Exact sciences and technology
Halides
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
N-alkylation
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Synthesis (chemistry)
Tetrahedrons
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Zusammenfassung:Herein, we report an efficient and facile synthesis of substituted 2-aminopyrroles from the reaction of enaminone–amidine adduct and various phenacyl, benzyl, or heteroalkyl halides in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in good to excellent yields. The reaction proceeds through an intramolecular 5-exo trig cyclization resulting into diversely substituted 2-aminopyrroles.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.08.149