A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination

Abstract

Michael addi cyanoacrylam further react 4-deazatoxofl reacting azae Unambiguous Cite this: Eur.

Cyclic Enaminone Incorporating 5‐cyanomethylpyrazole‐4‐carbonitrile: Unexpected Formation of Pyrazolo[l,5‐a]pyridine Derivatives

“…In continuation of our interest in the Michael addition reaction , we report herein the results of our investigations concerning the different reactivity patterns of substituted enamine 3 towards cinnamonitrile derivatives 4 . In the first step, 5‐(cyanomethyl)‐3‐((5,5‐dimethyl‐3‐oxocyclohex‐1‐en‐1‐yl)amino)‐1 H ‐pyrazole‐4‐carbonitrile 3 is prepared via the direct condensation reaction of dimedone 1 with the 3‐amino‐5‐(cyanomethyl)‐1 H ‐pyrazole‐4‐carbonitrile 2 using catalytic amount of trichloroacetic acid as a catalyst under solvent‐free conditions (Scheme ).…”

“…Enamines are versatile precursors and have several applications in the synthetic organic chemistry due to the nucleophilic character at β‐carbon . In addition, Michael addition is considered one of the most common reactions that leads to heterocycles through carbon–carbon bond formation . Moreover, pyrazolo[1,5‐ a ]pyridine scaffold represents a class of medicinally significant compounds, which has demonstrated a diverse range of bioactivities depending on the substitutions around the core pyridine ring.…”

Synthesis of novel hexahydroquinolines and 6‐amino‐2‐oxopyridine‐3,5‐dicarbonitriles incorporating sulfamethoxazole via [3 + 3] annulation

“…In continuation to our interest in the C─C bond formation reactions, the possibility of [3 + 3] atom combination reaction of the cyclic enamine incorporating sulfamethoxazole with α , β ‐unsaturated nitriles through Michael addition reaction was studied. First, the cyclic enamine 3 was prepared via the reaction of dimedone 1 with sulfamethoxazole 2 according to the procedure reported in the literature by us and by others (Scheme ).…”

Synthesis of Novel Bis(pyrido[2,1‐a]isoquinolines) Linked to Aliphatic or Aromatic Core via Ether Linkage

“…Due to their efficiency and simplicity, MCRs have been used in drug design . Recently, there has been an increased interest in the utility of Michael addition reaction in C ─ C bond formation reactions . In continuation to our efforts to simplify the synthesis of significant biologically active compounds , we report herein the syntheses of novel bis(azaphenanthrene) analogues via one‐pot three‐component reaction of bis(aldehydes) and malononitrile with 2‐(6,7‐dimethoxy‐3,4‐dihydroisoquinolin‐1‐yl)acetonitrile.…”