Synthesis of Small and Medium-Sized Ring Fused Quinazolinones
Doctor of Philosophy (Chemistry(International Program)), 2023
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Prince of Songkla University
2024
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| Online Access: | http://kb.psu.ac.th/psukb/handle/2016/19344 |
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th-psu.2016-193442024-01-25T08:22:16Z Synthesis of Small and Medium-Sized Ring Fused Quinazolinones การสังเคราะห์วงขนาดเล็กและขนาดกลางที่เชื่อมต่อกับควินาโซลิโนน Yotsakorn Saebang Juthanat Kaeobamrung Faculty of Science (Chemistry) คณะวิทยาศาสตร์ ภาควิชาเคมี tricyclic quinazolinones small-sized ring heterocycles medium-sized ring heterocycles copper-catalyzed domino reaction C-N bond formation Doctor of Philosophy (Chemistry(International Program)), 2023 Quinazolinones are natural alkaloids that play a crucial role in exhibiting a wide range of biological and pharmacological activities. Among them, ring-fused quinazolinones are commonly found in various natural alkaloids and synthetic molecules, showcasing a diverse array of bioactivities. In this study, we focused on synthesizing tricyclic quinazolinones. Medium and small-sized ring fused quinazolinones were achieved via direct cyclization of quinazolinone intermediates having tert-butyl ethylcarbamate and H as nitrogen substituents, respectively. Firstly, we focused on cyclic amine and urea moieties to fuse with quinazolinone skeletons to obtain novel 11-membered ring fused quinazolinones. Key intermediates were prepared through a copper-catalyzed domino reaction. We successfully incorporated an alkyl side chain with a functionalized amine moiety. The construction of the 11-membered ring urea moiety involved direct cyclization using 1,1'- carbonyldiimidazole (CDI) of a diamino quinazolinone intermediate, which was generated through a series of steps including reductive amination and Bocdeprotection. Secondly, we explored the synthesis of deoxyvasicinone derivatives, which are smaller-sized ring fused quinazolinones. The cyclization process for forming the smaller-sized ring was carried out under both basic and acidic conditions, resulting in the formation of two deoxyvasicinone analogues. Under basic conditions, 1-acetyl-2,3-dihydro pyrrolo[2,1-b]quinazolin-9(1H)-one analogues were synthesized via direct cyclization in the presence of I2. Under acidic conditions, we synthesized 1- acetylpyrrolo[2,1-b]quinazolin-9(3H)-one analogues through a two-step process involving α,α-dichlorination followed by intramolecular C–N bond cyclization, with para-toluene sulfonic acid (PTSA) serving as a catalyst. The developed synthetic strategies provide valuable insights into the preparation and modification of quinazolinone derivatives. 2024-01-25T08:22:16Z 2024-01-25T08:22:16Z 2023 Thesis http://kb.psu.ac.th/psukb/handle/2016/19344 en Attribution-NonCommercial-NoDerivs 3.0 Thailand http://creativecommons.org/licenses/by-nc-nd/3.0/th/ application/pdf Prince of Songkla University |
| institution |
Prince of Songkhla University |
| building |
Khunying Long Athakravi Sunthorn Learning Resources Center |
| continent |
Asia |
| country |
Thailand Thailand |
| content_provider |
Khunying Long Athakravi Sunthorn Learning Resources Center |
| collection |
PSU Knowledge Bank |
| language |
English |
| topic |
tricyclic quinazolinones small-sized ring heterocycles medium-sized ring heterocycles copper-catalyzed domino reaction C-N bond formation |
| spellingShingle |
tricyclic quinazolinones small-sized ring heterocycles medium-sized ring heterocycles copper-catalyzed domino reaction C-N bond formation Yotsakorn Saebang Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| description |
Doctor of Philosophy (Chemistry(International Program)), 2023 |
| author2 |
Juthanat Kaeobamrung |
| author_facet |
Juthanat Kaeobamrung Yotsakorn Saebang |
| format |
Theses and Dissertations |
| author |
Yotsakorn Saebang |
| author_sort |
Yotsakorn Saebang |
| title |
Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| title_short |
Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| title_full |
Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| title_fullStr |
Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| title_full_unstemmed |
Synthesis of Small and Medium-Sized Ring Fused Quinazolinones |
| title_sort |
synthesis of small and medium-sized ring fused quinazolinones |
| publisher |
Prince of Songkla University |
| publishDate |
2024 |
| url |
http://kb.psu.ac.th/psukb/handle/2016/19344 |
| _version_ |
1789484313274744832 |