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Synthesis of 4,5-diazaspiro[2.3]hexanes and 1,2-diazaspiro[3.3]heptanes as hexahydropyridazine analogues
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Pancholi, Alpa K., Iacobini, Greg P., Clarkson, Guy J., Porter, David and Shipman, Michael (2018) Synthesis of 4,5-diazaspiro[2.3]hexanes and 1,2-diazaspiro[3.3]heptanes as hexahydropyridazine analogues. The Journal of Organic Chemistry, 83 (1). pp. 491-498. doi:10.1021/acs.joc.7b02622 ISSN 0022-3263.
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WRAP-4-5-diazaspiro-2-3-hexanes-1-2-diazaspiro-3-3-heptanes-hexahydropyridazine-Pancholi-Shipman-2017.pdf - Accepted Version - Requires a PDF viewer. Download (1580Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.joc.7b02622
Abstract
4,5-Diazaspiro[2.3]hexanes are made by dihalocarbene addition across the exocyclic double bond of readily accessible 3-alkylidene-1,2-diazetidines. Using difluorocarbene, generated from TMSCF3/NaI, these spirocycles were produced in yields up to 97% by stereospecific addition across the alkene. Lower yields (up to 64%) were observed using more reactive dichlorocarbene, due to competitive insertion of the carbene into the NāN bond. Larger 1,2-diazaspiro[3.3]heptanes are produced by [2+2] cycloaddition of 3-alkylidene-1,2-diazetidines with tetracyanoethylene (TCNE) in up to 99% yield. These additions work with di-, tri- and tetrasubstituted alkenes, offering a practical route to rigidified analogues of the medicinally important hexahydropyridazines.
| Item Type: | Journal Article | ||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry | ||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Heterocyclic compounds, Pharmaceutical chemistry | ||||||||||||||||||
| Journal or Publication Title: | The Journal of Organic Chemistry | ||||||||||||||||||
| Publisher: | American Chemical Society | ||||||||||||||||||
| ISSN: | 0022-3263 | ||||||||||||||||||
| Official Date: | 5 January 2018 | ||||||||||||||||||
| Dates: |
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| Volume: | 83 | ||||||||||||||||||
| Number: | 1 | ||||||||||||||||||
| Page Range: | pp. 491-498 | ||||||||||||||||||
| DOI: | 10.1021/acs.joc.7b02622 | ||||||||||||||||||
| Status: | Peer Reviewed | ||||||||||||||||||
| Publication Status: | Published | ||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||
| Date of first compliant deposit: | 4 December 2017 | ||||||||||||||||||
| Date of first compliant Open Access: | 28 November 2018 | ||||||||||||||||||
| RIOXX Funder/Project Grant: |
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