Academic Journal
Diversity‐Oriented Synthesis of 2‐Iminothiazolidines: Pushing the Boundaries of the Domino Nucleophilic Displacement/Intramolecular anti‐Michael Addition Process
| العنوان: | Diversity‐Oriented Synthesis of 2‐Iminothiazolidines: Pushing the Boundaries of the Domino Nucleophilic Displacement/Intramolecular anti‐Michael Addition Process |
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| المؤلفون: | Ferreira, Misael, Munaretto, Laiéli S., Gouvêa, Daniela P., Bortoluzzi, Adailton J., Sá, Marcus M. |
| المساهمون: | Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior |
| المصدر: | European Journal of Organic Chemistry ; volume 2022, issue 15 ; ISSN 1434-193X 1099-0690 |
| بيانات النشر: | Wiley |
| سنة النشر: | 2022 |
| المجموعة: | Wiley Online Library (Open Access Articles via Crossref) |
| الوصف: | Methods for the synthesis of a variety of functionalized 2‐iminothiazolidines and related heterocycles through a base‐mediated domino nucleophilic displacement/intramolecular anti ‐Michael addition process involving electron‐deficient allylic bromides and 1,3‐ambident nucleophiles derived from thiourea were developed. These transformations proceed under mild and simple conditions and different functional groups are well tolerated. The scope and limitations of this protocol are dependent on the structure of the allylic bromide and 1,3‐ambident nucleophile involved. The synthetic versatility of 2‐iminothiazolidines was further demonstrated through a series of chemoselective modifications, giving rise to a wide range of thiazolidine frameworks of structural complexity. In particular, the reductive cyclization of 2‐nitrobenzyl‐substituted 2‐iminothiazolidines furnished novel spiroquinolones in good to fair yields. The structural assignment of key products was unequivocally achieved by X‐ray diffraction analysis and two‐dimensional NMR techniques. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| DOI: | 10.1002/ejoc.202101562 |
| الاتاحة: | http://dx.doi.org/10.1002/ejoc.202101562 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202101562 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejoc.202101562 |
| Rights: | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| رقم الانضمام: | edsbas.3A9BDC8F |
| قاعدة البيانات: | BASE |
| DOI: | 10.1002/ejoc.202101562 |
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