Michael addition/pericyclization/rearrangement – a multicomponent strategy for the synthesis of substituted resorcinols

Abstract

The combination of methyl 3,7-dioxo-2-diazo-4-octenoate from the zinc triflate catalyzed Mukaiyama-Michael reaction of methyl 3-tert-butylsilyloxy-2-diazobutenoate and 4-methoxy-3-buten-2-one with Michael acceptors (methyl vinyl ketone, N-phenylmaleimide, β-nitrovinylarenes) in the presence of a catalytic amount of base provides convenient access to highly substituted resorcinol derivatives. This transformation is achieved in an efficient one-pot multi-component transformation by the sequential addition of the reagents.

Microwave assisted L‐proline catalyzed one‐pot three–component reaction for the synthesis of 4‐aminoaryl‐2‐phenyl‐2H‐3‐nitrochromene hybrid via Domino Michael‐Henry‐Michael addition reaction

“…Instead of this Et 2 NH, Et 3 N and pyridine were ineffective in the given protocol and trace or no product was detected (Table 1, entries 11-13). We had additionally tested the impact of various solvents including DMF, DME, THF, ACN, 1,2 DCE, NMP, Toluene, EtOH and EtOH:H 2 O (Table 1, entries [14][15][16][17][18][19][20][21][22]. Solvents such as DMF and DME gave less yield of the product 4aa (Table 1, entries 14 and 15).…”

“…Among all these reactions, Michael addition reaction proved to be versatile reaction and commonly used in various organic transformations using multicomponent reaction [17]. Several multicomponent reactions were reported using Michael addition strategy [18]. Thierry Constantieux et al reported metal free Michael addition‐initiated three‐component reaction for regioselective synthesis of functionalized pyridines from ammonium acetate, 1,3 dicarbonyl compounds and acrolein [19].…”

“…Nowadays, microwave irradiation is widely used for the conversion of organic matter because of various advantage of microwave radiation over conventional heating such as reduction of reaction time from hours to minutes, reduction of wastage and usually microwave irradiation reduces the side reaction via increasing the product yield [21]. Thus, microwave technique is a valuable alternative over conventional heating, introduces energetic radiations into the reaction and thereby enhances the reaction rate [18,19].…”

Biomimetic Synthesis of Functionalized γ‐Resorcylates from Dioxinone Derivatives

“…Specifically, 3,5‐Di‐ tert ‐butyl‐γ‐resorcylic acid and its ester derivatives have shown effectiveness against platelet aggregation and atherosclerosis whereas the naturally occurring γ‐resorcylate penicillide and its derivatives have shown biological activity including inhibition of cholesterol ester transfer protein and oxytocin antagonism 2. Efficient syntheses of functionalized resorcinols from resorcinol (1,3‐hydroxybenzene) can be problematical and, as such, syntheses from non‐aromatic precursors may be used as alternatives 3. Such syntheses of γ‐resorcylates are currently limited but an example from the work of Doyle is summarized in Scheme 4…”

Copper/Silver Cocatalyzed Regioselective C5–H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds

“…The C-C bond is one of the most fundamental and common types of bond in organic compounds. 1 Several classic organic reactions such as nucleophilic addition, 2 nucleophilic substitution, 3 the Friedel-Crafts reaction, 4 and pericyclization 5 have been developed as conventional methods for C-C bond construction. As research progressed in this field, transition-metal-catalyzed C-C bond formation has attracted significant attention.…”