The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

Beilstein Journal of Organic Chemistry

Cherie A. Motti¹  Ashfaq Mahmood Qureshi²  Anke Nietsch³  Gaetano Saya⁴  Peter C. Junk⁴  Ommid Anamimoghadam⁴  Saira Mumtaz⁴  Jun Wang⁴  Michael Oelgemöller⁴ 

[1] Australian Institute of Marine Science, Townsville, Queensland, Australia;Bahauddin Zakariya University, Institute of Chemical Sciences, Multan, Pakistan;Dublin City University, School of Chemical Sciences, Dublin 9, Ireland;James Cook University, College of Science and Engineering, Townsville, Queensland 4811, Australia;

关键词: anesthetics;    arylmethylenedihydroisoindolinones;    photochemistry;    photodecarboxylation;    phthalimide;   

DOI  :  10.3762/bjoc.13.275

来源: DOAJ

【 摘 要 】

The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to N-(bromoalkyl)phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms.

【 授权许可】

Unknown