Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization
In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered...
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| Published in | Advanced science Vol. 11; no. 40; pp. e2407931 - n/a |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
John Wiley & Sons, Inc
01.10.2024
John Wiley and Sons Inc Wiley |
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| Abstract | In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O‐ to N‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O‐attack route.
Taking advantage of the unique ring‐opening properties of cyclopropenes, a versatile and efficient approach toward benzo‐fused five‐membered oxa‐ and aza‐heterocycles from the same raw materials is reported. With this practical method, a potential PD‐L1 down‐regulator with a novel isobenzofuranone O‐alkyl oxime moiety is synthesized. |
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| AbstractList | In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O‐ to N‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O‐attack route. In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O‐ to N‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O‐attack route. Taking advantage of the unique ring‐opening properties of cyclopropenes, a versatile and efficient approach toward benzo‐fused five‐membered oxa‐ and aza‐heterocycles from the same raw materials is reported. With this practical method, a potential PD‐L1 down‐regulator with a novel isobenzofuranone O‐alkyl oxime moiety is synthesized. In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O ‐ to N ‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O ‐attack route. Taking advantage of the unique ring‐opening properties of cyclopropenes, a versatile and efficient approach toward benzo‐fused five‐membered oxa‐ and aza‐heterocycles from the same raw materials is reported. With this practical method, a potential PD‐L1 down‐regulator with a novel isobenzofuranone O ‐alkyl oxime moiety is synthesized. Abstract In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo‐fused five‐membered oxa‐ and aza‐heterocycles through a formal [4+1] cyclization and subsequent acid‐catalyzed intramolecular O ‐ to N ‐ rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late‐stage modification of complex molecules and in the synthesis of a potential PD‐L1 gene down‐regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)‐mediated sequential C─H coupling/π‐allylation/dynamically favorable O ‐attack route. |
| Author | Wu, Yuanqing Ding, Ning Lin, Binyan Zhan, Qichen Peng, Zhi‐Huan Zhou, Zhi Liu, Shijie Cao, Tao Gu, Fengyan Luo, Mei Cao, Peng |
| AuthorAffiliation | 2 State Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture Nanjing University of Chinese Medicine Nanjing Jiangsu 210023 China 5 The Quzhou Affiliated Hospital of Wenzhou Medical University Quzhou People's Hospital Quzhou Zhejiang 324000 China 6 Gaoyou Hospital of Traditional Chinese Medicine Yangzhou Jiangsu 225600 China 4 Jiangsu Provincial Medicinal Innovation Center Affiliated Hospital of Integrated Traditional Chinese and Western Medicine Nanjing University of Chinese Medicine Nanjing Jiangsu 210028 China 1 School of Pharmacy Nanjing University of Chinese Medicine Nanjing Jiangsu 210023 China 3 Key Laboratory of Molecular Target and Clinical Pharmacology & State Key Laboratory of Respiratory Disease School of Pharmaceutical Sciences & the Fifth Affiliated Hospital Guangzhou Medical University Guangzhou Guangdong 511436 China |
| AuthorAffiliation_xml | – name: 3 Key Laboratory of Molecular Target and Clinical Pharmacology & State Key Laboratory of Respiratory Disease School of Pharmaceutical Sciences & the Fifth Affiliated Hospital Guangzhou Medical University Guangzhou Guangdong 511436 China – name: 4 Jiangsu Provincial Medicinal Innovation Center Affiliated Hospital of Integrated Traditional Chinese and Western Medicine Nanjing University of Chinese Medicine Nanjing Jiangsu 210028 China – name: 5 The Quzhou Affiliated Hospital of Wenzhou Medical University Quzhou People's Hospital Quzhou Zhejiang 324000 China – name: 6 Gaoyou Hospital of Traditional Chinese Medicine Yangzhou Jiangsu 225600 China – name: 1 School of Pharmacy Nanjing University of Chinese Medicine Nanjing Jiangsu 210023 China – name: 2 State Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture Nanjing University of Chinese Medicine Nanjing Jiangsu 210023 China |
| Author_xml | – sequence: 1 givenname: Fengyan surname: Gu fullname: Gu, Fengyan organization: Nanjing University of Chinese Medicine – sequence: 2 givenname: Binyan surname: Lin fullname: Lin, Binyan organization: Nanjing University of Chinese Medicine – sequence: 3 givenname: Zhi‐Huan surname: Peng fullname: Peng, Zhi‐Huan organization: Guangzhou Medical University – sequence: 4 givenname: Shijie surname: Liu fullname: Liu, Shijie organization: Nanjing University of Chinese Medicine – sequence: 5 givenname: Yuanqing surname: Wu fullname: Wu, Yuanqing organization: Nanjing University of Chinese Medicine – sequence: 6 givenname: Mei surname: Luo fullname: Luo, Mei organization: Nanjing University of Chinese Medicine – sequence: 7 givenname: Ning surname: Ding fullname: Ding, Ning organization: Nanjing University of Chinese Medicine – sequence: 8 givenname: Qichen surname: Zhan fullname: Zhan, Qichen organization: Nanjing University of Chinese Medicine – sequence: 9 givenname: Peng surname: Cao fullname: Cao, Peng email: cao_peng@njucm.edu.cn organization: Gaoyou Hospital of Traditional Chinese Medicine – sequence: 10 givenname: Zhi surname: Zhou fullname: Zhou, Zhi email: zhouzhi@gzhmu.edu.cn organization: Guangzhou Medical University – sequence: 11 givenname: Tao orcidid: 0000-0002-8309-5695 surname: Cao fullname: Cao, Tao email: caot@njucm.edu.cn organization: Nanjing University of Chinese Medicine |
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| Keywords | late‐stage modifications cyclopropenes ring transformation heterocycles DFT calculations rhodium |
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| Snippet | In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged.... Abstract In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have... |
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| SubjectTerms | Carbon cyclopropenes DFT calculations heterocycles late‐stage modifications Ligands Nitrogen rhodium ring transformation |
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| Title | Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization |
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