Facile Synthesis of Dispiroheterocycles through One-Pot [3+2] Cycloaddition, and Their Antiviral Activity

Abstract

A facile synthesis of novel dispiroheterocycles has been developed through one-pot [3+2] cycloaddition between isatins, amino acids, and aurones. Thirty different dispiroheterocycles were synthesized eusing this method which features mild conditions, convenient operation, and high efficacy. Evaluation of the bioactivity of these dispiroheterocyclic products revealed antiviral activity against tobacco mosaic virus (TMV).

The application of isatin-based multicomponent-reactions in the quest for new bioactive and druglike molecules

“…The antiviral activity of these compounds was evaluated against tobacco mosaic virus (TMV) (Scheme 45B). Compound 149 displayed similar antiviral activity to the commercially available natural compound ningnanmycin [145], which can induce tobacco plant defense mechanisms against TMV [146]. This shows the potential of MCR-obtained oxindole derivatives as potent agrochemicals.…”

Decade Advance of Isatin in Three‐component Reactions

“…Azomethine ylide intermediates could be generated in situ from decarboxylative condensation of isatins and α ‐amino acids [19a–g] . α ‐Amino acids like N ‐alkyl glycines [19a,e] and sarcosine [19b–d,f] were frequently employed for the synthesis of spirooxindoles 19.1 via a similar mechanism. Condensation 19.2 , esterification 19.3 , decarboxylation 19.4 and 1,3‐dipolar cycloaddition 19.5 were involved during the process.…”

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

“…A very similar approach was reported by Zhang et al ., but replacing the dipolarophile by aurones and expanding the scope to three different secondary amino acids – sarcosine (Scheme 13A), D ‐proline and thioproline (Scheme 13B). The library of dispiroheterocycles (30 examples) was achieved in moderate to good yields [39] …”