AI Article Synopsis
- A new method has been developed for creating diazepine-containing spiroindolines using a base-promoted annulation reaction involving α-halogenated acylhydrazones and isatin-derived MBH carbonates.
- The reaction mechanism is a complex process that includes generating an allylic ylide, nucleophilic substitution, Michael addition, and elimination.
- This synthetic protocol allows for a variety of highly functionalized spiro[indoline-3,5'-[1,2]diazepines] to be produced efficiently and features broad substrate compatibility along with straightforward reaction conditions.
Article Abstract
A straightforward synthetic protocol for the efficient construction of diazepine-containing spiroindolines has been developed and proceeds through a by base-promoted annulation reaction of α-halogenated -acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3] annulation includes the in situ generated allylic ylide, nucleophilic substitution, Michael additon, and elimination processes. Additionally, the similar reaction with α-halogenated -tosylhydrazones also afforded -tosyl-substituted spiro[indoline-3,5'-[1,2]diazepine] in satisfactory yields. This protocol provides a convenient approach for the assembly of diverse highly functionalized spiro[indoline-3,5'-[1,2]diazepines] and also features a broad substrate scope, simple reaction conditions, and high molecular convergence.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10760482 | PMC |
| http://dx.doi.org/10.3762/bjoc.19.143 | DOI Listing |
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