Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented sy...
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| Format: | Article |
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MDPI AG
2023-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/19/6761 |
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| author | Kaikai Wang Wenwen Zhou Jun Jia Junwei Ye Mengxin Yuan Jie Yang Yonghua Qi Rongxiang Chen |
| author_facet | Kaikai Wang Wenwen Zhou Jun Jia Junwei Ye Mengxin Yuan Jie Yang Yonghua Qi Rongxiang Chen |
| author_sort | Kaikai Wang |
| collection | DOAJ |
| description | Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 <i>dr</i>). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2′-[1,3]oxazino[2,3-<i>a</i>]isoquinoline] and spiro[indene-2,1′-pyrrolo[2,1-<i>a</i>]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis. |
| first_indexed | 2024-03-10T21:39:45Z |
| format | Article |
| id | doaj.art-64dda8a4327548c0b91794f668cf61ab |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:39:45Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-64dda8a4327548c0b91794f668cf61ab2023-11-19T14:45:13ZengMDPI AGMolecules1420-30492023-09-012819676110.3390/molecules28196761Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-DihydroisoquinolinesKaikai Wang0Wenwen Zhou1Jun Jia2Junwei Ye3Mengxin Yuan4Jie Yang5Yonghua Qi6Rongxiang Chen7School of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaJilin Province Product Quality Supervision and Inspection Institute, Changchun 130012, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Chemistry & Materials Engineering, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSchool of Pharmacy, Xinxiang University, Xinxiang 453000, ChinaSubstrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 <i>dr</i>). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2′-[1,3]oxazino[2,3-<i>a</i>]isoquinoline] and spiro[indene-2,1′-pyrrolo[2,1-<i>a</i>]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis.https://www.mdpi.com/1420-3049/28/19/6761substrate-controlledninhydrin-derived MBH adducts3,4-dihydroisoquinolinescycloadditionpolycyclic frameworksDiels-Alder reaction |
| spellingShingle | Kaikai Wang Wenwen Zhou Jun Jia Junwei Ye Mengxin Yuan Jie Yang Yonghua Qi Rongxiang Chen Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines Molecules substrate-controlled ninhydrin-derived MBH adducts 3,4-dihydroisoquinolines cycloaddition polycyclic frameworks Diels-Alder reaction |
| title | Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines |
| title_full | Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines |
| title_fullStr | Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines |
| title_full_unstemmed | Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines |
| title_short | Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines |
| title_sort | substrate controlled diversity oriented synthesis of novel polycyclic frameworks via 4 2 and 3 2 annulations of ninhydrin derived mbh adducts with 3 4 dihydroisoquinolines |
| topic | substrate-controlled ninhydrin-derived MBH adducts 3,4-dihydroisoquinolines cycloaddition polycyclic frameworks Diels-Alder reaction |
| url | https://www.mdpi.com/1420-3049/28/19/6761 |
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