Nitroketenaminale, 5. Mitt.: Synthese von N²‐substituierten 2‐Amino‐3‐nitropyridinen als Vorstufen von Pyrido[2,3‐b]pyrazinen (3‐Desazapteridinen)

Abstract

N2‐substituierte 2‐Amino‐3‐nitropyridine lassen sich aus den Nitroketenaminalen 3 und 1,3‐Biselektrophilen wie 1 und 2 herstellen. Durch Oxidation und anschließende katalytische Hydrierung von 13 gelangt man zum 1,2,3,4‐Tetrahydropyrido[2,3‐b]pyrazin 17.

Highly Selective Synthesis of 2-Amino-4,6-diarylpyridine Derivatives by the Cascade Reaction of 1,1-Enediamines with α,β-Unsaturated Ketones

“…However, acyclic 1,1-enediamines (EDAMs) have not been considered for many years. Rare studies have shown that EDAMs serve as bisnucleophiles (α-carbon and N as nucleophilic sites) and react with biselectrophiles to produce fused heterocyclic compounds. , In continuation of our interest in the synthesis of functionalized heterocyclic compounds with pharmacological activity and from available building blocks, we aim to use EDAMs as building blocks to construct novel 2-amino-4,6-diarylpyridine ring systems (Scheme ). Using the N(3) of EDAMs 2 to attack the electrophilic sites shows little steric effect ((N3) vs NHAr).…”

Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1H-indene-1,3(2H)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds

“…1,1-Enediamines (EDAMs) are fascinating and versatile building blocks that are widely used to synthesize various fused heterocyclic compounds. − We have used EDAMs as bisnucleophilic reagents to react with isatins via a cascade reaction for the synthesis of indenopyridine derivatives , (Scheme ). Other researchers have used a diversity of enamines as substrates for the synthesis of various indenopyridine derivatives through cascade reactions. − Based on the importance of indenopyridine derivatives, we explored the cascade of EDAMs for synthesis of indenopyridine derivatives including indenopyridines and IDDPs.…”

Diastereoselective Synthesis of Morphan Derivatives by Michael and Hetero-Michael Addition of 1,1-Enediamines to Quinone Monoketals

“…However, acyclic EDAMs have not been considered for many years. Seldom literature reports have shown that EDAMs serve as bisnucleophiles (α-carbon and N as nucleophilic sites) and react with biselectrophiles to produce fused heterocyclic compounds . To date, to the best of our knowledge, incorporation of the two nucleophilic sites (α-C and N) through the Michael and hetero-Michael addition of EDAMs to form bridged-ring frame compounds has not been reported.…”