The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

Abstract

The regioselective three-component condensation of azomethine ylides derived from isatins and α-amino acids with acrylamides or aroylacrylic acids as dipolarophiles has been realized through a one-pot 1,3-dipolar cycloaddition protocol. Decarboxylation of 2'-aroyl-2-oxo-1,1',2,2',5',6',7',7a'-octahydrospiro[indole-3,3'-pyrrolizine]-1'-carboxylic acids is accompanied by cyclative rearrangement with formation of dihydropyrrolizinyl indolones.117

Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents

“…Chalcone bears a very good synthon so that varieties of novel heterocycles with good pharmaceutical profile can be designed [4,5,6]. An interesting feature of this structure is a pincer-like conformation of the molecule [26], and a reaction between isatin and the α-amino acid afforded the azomethine ylide, with regioselective addition to the C=C bond of aroylacrylic acid or chalcone. The electrophilic centers in 4 can be allowed to react with simply bi-nucleophiles, e.g., hydrazine derivatives and hydroxyl amine, to afford important spiro heterocyclic compounds [19].…”

Molecular diversity of spirooxindoles. Synthesis and biological activity

“…Aroylacrylic acids 153 were for the first time successfully used in this three-component reaction as unsymmetrical dipolarophiles [92]. The domino-reaction of dipolarophiles 153 with isatins 114 and sarcosine 63/proline 74 led to spiropyrrolidines 154 and spiropyrrolizidines 155 in moderate to good yields.…”

Ecofriendly synthesis of pyrano[2,3‐d]pyrimidine derivatives and related heterocycles with anti‐inflammatory activities

“…[22] In connection to our previous studies on the biological activities of pyrimidine and fused derivatives, [23][24][25][26][27] the one-pot reaction has become significant in combinatorial and green chemistry due to its process simplicity, mild conditions, atomic economy, and extension of the scope of substrates. [28] So, the authors decided to synthesize the pyranopyrimidine derivatives through a nanoparticle catalyst, which has revealed broad applications as a facile and efficient method to carry out many organic reactions, producing high yields and higher selectivity, lower quantities of side products, and consequently, easier workup and purification of the products, and designing polyheterocyclic compounds containing five and/or six rings fused with each other so as to obtain a superior biological activity. Table 1).…”