Chemoselective and Regiospecific Synthesis of Iminospiro‐<i>γ</i>‐lactones from Maleic Anhydride or Citraconic Anhydride and Alkyl Isocyanides with Dialkyl Acetylenedicarboxylates

Bayat, Mohammad; Imanieh, Hossein; Abbasi, Hossien

doi:10.1002/hlca.200900292

Cited by 10 publications

(1 citation statement)

References 21 publications

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“…The model compound (MC) synthesized from reactants cyclohexyl isocyanide 4, 2, and 3d under reaction conditions similar to MCSP was created to clearly confirm the structure of the target spiropolymers. According to reported small-molecule reactions and our previous work, 33,34,47 we believe that the zwitterionic intermediate formed by isocyanide and monomer 2 will undergo a nucleophilic addition reaction with the unsaturated C�O of different anhydrides to obtain spirocompounds (Scheme 1B), leading to the possibility of isomers. As shown in Scheme 2, trans-MC with 30% yield and cis-MC with 41% yield were successfully obtained by the model reaction, as expected.…”

Section: Structural Characterizationmentioning

confidence: 91%

Multicomponent Spiropolymerization of Diisocyanides, Activated Alkynes, and Bis-Anhydrides

Zhu

Lin

et al. 2022

Macromolecules

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Among various polymerization reactions, multicomponent spiropolymerization (MCSP) based on diisocyanides, activated alkynes, and a third monomer is an important tool for the in situ synthesis of multifunctional spiropolymers. In this work, a new MCSP based on the selection of bis-anhydrides as a third monomer was successfully developed under mild conditions. The obtained spiropolymers have high molecular weights (M w up to 92,600 g/mol) and yields (up to 92%), as well as good solubilities and thermal stabilities. The benzophenone-containing spiropolymer P1a3e with aggregation-induced emission characteristics exhibits good UV-irradiation degradation performance, making it potentially applicable as a photoresist material component. Moreover, the spiropolymer P1a3f containing the acid-sensitive iminofuran ring is able to be degraded by a strong acid, while its postmodified product P1a3f-SH has higher degradation efficiency because of the enhanced water solubility. The results reveal that both P1a3f and P1a3f-SH with low cytotoxicities could potentially be used as acid-promoted release carriers of drugs for the protection of gastric mucosa. Therefore, this reaction enriches the family of MCSP reactions for preparing multifunctional spiropolymers, which accelerates the development of polymerization methodology.

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Section: Structural Characterizationmentioning

confidence: 91%