Microwave Assisted Neat Synthesis of Spiropyrrolidine Library

Abstract

A new class of functionalized nitrothiophene containing spirropyrrolidines has been synthesized with high regioselectivity in moderate to excellent yields via microwave assisted solvent‐free‐three component 1,3‐dipolar cycloaddition reaction of in situ generated azomethineylides with various substituted chalcones as dipolarophiles. The structures of the newly synthesized compounds were established by analytical and spectral analysis. The product yields were slightly improved and reaction times were reduced to a great extent under microwave condition.

Synthesis of chalcone precursor via Cu(I) catalyzed 1,3‐dipolar reaction of functionalized acetylene and pyrazole embedded dipole

“…The copper (I)‐catalyzed 1,4‐substituted‐1,2,3‐triazole forming reaction between azides and alkynes has become the gold standard of “click chemistry” due to its accuracy, specificity, and biocompatibility and gained remarkable utility in the development of novel lead molecules. [ 28 ] Owing to these observations and in continuation of our research work on the synthesis of biologically active heterocycles [ 29–31 ] through dipolar cycloaddition [ 32,33 ] herein we report the synthesis and biological activity of 1,2,3‐triazole through copper‐mediated click chemistry (Figure 1).…”

One‐pot three‐component 1,3‐dipolar cycloaddition of azomethineylides to nitrofuran containing acetylenic ketones and molecular docking studies of the cycloadducts

“…Previously we have reported the 1,3‐dipolar cycloaddition of azomethineylides generated from ninhydrin and sarcosine with furan containing and 5‐nitrofuran containing chalcones (Scheme 1). [ 18–20 ]…”

“…[ 18 ] However, the introduction of a nitro group into the 5th position of the furan ring turns it to a highly regioselective one (Scheme 1b). [ 19,20 ]…”

1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst

“…These features convert this cycloaddition in a very attractive subject for implementing the green chemistry concepts. The ability to run these reactions using multicomponent versions [8] and the employment of more efficient microwave-assisted heating, [9,10] were also adapted. For example, heterogeneous graphene oxide, [4] zinc oxide nanoparticles, [5] heterogeneous silver nanoparticle, [6] bentonite, [7] were used as a recyclable catalyst.…”

“…For example, heterogeneous graphene oxide, [4] zinc oxide nanoparticles, [5] heterogeneous silver nanoparticle, [6] bentonite, [7] were used as a recyclable catalyst. The ability to run these reactions using multicomponent versions [8] and the employment of more efficient microwave-assisted heating, [9,10] were also adapted. Sequential thermal (MW) [3+2] cycloaddition involving imino esters generated in situ was also efficient in a multicomponent fashion.…”