Tsuji-Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines
| العنوان: | Tsuji-Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines |
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| المؤلفون: | Thomas W. Bell, Nicholas C. Pflug, Sreenivasa Anugu, Florian Goulinet-Mateo, Katrin Lamprecht, Reena Chawla, Rameez Ali, Violeta G. Demillo, Emily D. Scarbrough, Sunil Hamal, Alekhya Sama, Sagar Gyawali, Truc D. T. Le, Liezel A. Lumangtad, Dylan E. Jones |
| المصدر: | ACS Omega, 4 (1) ACS Omega, Vol 4, Iss 1, Pp 1254-1264 (2019) ACS Omega |
| بيانات النشر: | American Chemical Society, 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | 010405 organic chemistry, General Chemical Engineering, General Chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Article, 3. Good health, 0104 chemical sciences, lcsh:Chemistry, chemistry.chemical_compound, chemistry, lcsh:QD1-999, Pyridine |
| الوصف: | Macrocyclic triamine disulfonamides can be synthesized by double Tsuji–Trost N-allylation reaction of open-chain disulfonamides with 2-alkylidene-1,3-propanediyl bis(carbonates). The previously used Atkins–Richman macrocyclization method generally gives lower yields and requires more tedious purification of the product. Solvent, palladium source, ligand, and concentration have all been varied to optimize the yields of two key 12-membered ring bioactive compounds, CADA and VGD020. The new approach tolerates a wide range of functional groups and gives highest yields for symmetrical compounds in which the acidities of the two sulfonamide groups are matched, although the yields of unsymmetrical compounds are still generally good. The method has also been extended to the synthesis of 11-membered rings, pyridine-fused macrocycles, and products bearing an ester or aryl substituent on the exocyclic double bond. ISSN:2470-1343 |
| وصف الملف: | application/application/pdf |
| اللغة: | English |
| تدمد: | 2470-1343 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::168293d30a812016f387b7d87a176d1c https://hdl.handle.net/20.500.11850/322310 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....168293d30a812016f387b7d87a176d1c |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 24701343 |
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