Interception and Synthetic Application of Diradical and Diene Forms of Dual‐Nature Azabicyclic o‐Quinodimethanes Generated by 6π‐Azaelectrocyclization Article Swipe
Shankar Majji
,
Daniel Lee
,
Supuni I. N. Hewa Inaththappulige
,
Ayush Acharya
,
Hemant P. Yennawar
,
Ramesh Giri
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202409613
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1002/anie.202409613
We demonstrate that 2‐alkenylarylaldimines and ketimines undergo thermal 6π‐azaelectrocyclization to generate a wide range of azabicyclic o ‐quinodimethanes ( o ‐QDMs). These o ‐QDMs exist as a hybrid of a diene and a benzylic diradical. The diradical nature was confirmed by their ability to undergo dimerization and react with H‐atom donor, 2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO) and O 2 . In addition, the interception of the diradicaloid o ‐QDMs by H‐atom transfer was used to synthesize five tetrahydroisoquinoline alkaloids and related bioactive molecules. The diene form can undergo [4+2] cycloaddition reactions with different dienophiles to generate bridged azabicycles in high endo:exo selectivity. The azabicyclic o ‐QDMs can be generated for [4+2] cycloaddition from a wide range of electronically and sterically varied 2‐alkenylarylimines, including mono, di, tri and tetrasubstituted alkenes, and imines derived from arylamine, alkylamine (1°, 2°, 3°), benzylamine, benzylsulfonamide and Boc ‐amine.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1002/anie.202409613
- OA Status
- green
- Cited By
- 1
- References
- 59
- Related Works
- 10
- OpenAlex ID
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https://doi.org/10.1002/anie.202409613Digital Object Identifier
- Title
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Interception and Synthetic Application of Diradical and Diene Forms of Dual‐Nature Azabicyclic o‐Quinodimethanes Generated by 6π‐AzaelectrocyclizationWork title
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articleOpenAlex work type
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enPrimary language
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2024Year of publication
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2024-07-18Full publication date if available
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Shankar Majji, Daniel Lee, Supuni I. N. Hewa Inaththappulige, Ayush Acharya, Hemant P. Yennawar, Ramesh GiriList of authors in order
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https://doi.org/10.1002/anie.202409613Publisher landing page
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
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https://pmc.ncbi.nlm.nih.gov/articles/PMC12038820/Direct OA link when available
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Diradical, Interception, Dual (grammatical number), Diene, Chemistry, Computational chemistry, Organic chemistry, Physics, Ecology, Philosophy, Biology, Singlet state, Quantum mechanics, Excited state, Linguistics, Natural rubberTop concepts (fields/topics) attached by OpenAlex
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1Total citation count in OpenAlex
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2025: 1Per-year citation counts (last 5 years)
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10Other works algorithmically related by OpenAlex
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