A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory
A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in t...
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| Format: | Article |
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Frontiers Media S.A.
2019-08-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00584/full |
| _version_ | 1811221312243236864 |
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| author | Huihui Yan Huihui Yan Xu-Qiong Xiao Robert C. Hider Yongmin Ma Yongmin Ma |
| author_facet | Huihui Yan Huihui Yan Xu-Qiong Xiao Robert C. Hider Yongmin Ma Yongmin Ma |
| author_sort | Huihui Yan |
| collection | DOAJ |
| description | A new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1. |
| first_indexed | 2024-04-12T07:57:12Z |
| format | Article |
| id | doaj.art-fc8c8c3a41464fcfaf9c0d2947b49b8d |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-12T07:57:12Z |
| publishDate | 2019-08-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-fc8c8c3a41464fcfaf9c0d2947b49b8d2022-12-22T03:41:27ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-08-01710.3389/fchem.2019.00584480021A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and TheoryHuihui Yan0Huihui Yan1Xu-Qiong Xiao2Robert C. Hider3Yongmin Ma4Yongmin Ma5School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, ChinaSchool of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, ChinaKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, ChinaInstitute of Pharmaceutical Science, King's College London, London, United KingdomSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, ChinaSchool of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, ChinaA new series of 3-substituted 4-methylene-quinazolinthiones and 4-methylene-quinazolinones were synthesized in moderate to excellent yield through a simple reaction of 2-aminoacetophenones with isocyanates or isothiocyanates. The reaction shows good tolerance of many important functional groups in the presence of air and water under metal-free conditions. Only water is produced as a coproduct, rendering this “green” methodology a highly versatile and eco-friendly alternative to the existing methods for the construction of the quinazolinone/quinazolinthione framework. We have interpreted the reaction mechanism by use of quantum chemical calculations on the basis of state-of-the-art computational methods SMD-B3LYP-D3(BJ)/BS1//B3LYP/BS1.https://www.frontiersin.org/article/10.3389/fchem.2019.00584/fullcyclizationquinazolinonequinazolinthionequantum chemical calculationsSMD-B3LYP |
| spellingShingle | Huihui Yan Huihui Yan Xu-Qiong Xiao Robert C. Hider Yongmin Ma Yongmin Ma A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory Frontiers in Chemistry cyclization quinazolinone quinazolinthione quantum chemical calculations SMD-B3LYP |
| title | A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory |
| title_full | A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory |
| title_fullStr | A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory |
| title_full_unstemmed | A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory |
| title_short | A Simple Metal-Free Cyclization for the Synthesis of 4-Methylene-3-Substituted Quinazolinone and Quinazolinthione Derivatives: Experiment and Theory |
| title_sort | simple metal free cyclization for the synthesis of 4 methylene 3 substituted quinazolinone and quinazolinthione derivatives experiment and theory |
| topic | cyclization quinazolinone quinazolinthione quantum chemical calculations SMD-B3LYP |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00584/full |
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