Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues
1
2
Novartis
Institutes for BioMedical Research, Horsham Research Centre, Wimblehurst
Road, West Sussex, RH12
5AB, United Kingdom
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Publication type: Journal Article
Publication date: 2017-12-11
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
29183129
Organic Chemistry
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 N-N 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.
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Total citations:
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Citations from 2024:
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(44.44%)
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Pancholi A. K. et al. Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues // Journal of Organic Chemistry. 2017. Vol. 83. No. 1. pp. 491-498.
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Pancholi A. K., Iacobini G. P., Clarkson G. J., Porter D. W., Shipman M. Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues // Journal of Organic Chemistry. 2017. Vol. 83. No. 1. pp. 491-498.
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TY - JOUR
DO - 10.1021/acs.joc.7b02622
UR - https://doi.org/10.1021/acs.joc.7b02622
TI - Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues
T2 - Journal of Organic Chemistry
AU - Pancholi, Alpa K
AU - Iacobini, Greg P
AU - Clarkson, Guy J.
AU - Porter, David W
AU - Shipman, Michael
PY - 2017
DA - 2017/12/11
PB - American Chemical Society (ACS)
SP - 491-498
IS - 1
VL - 83
PMID - 29183129
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Pancholi,
author = {Alpa K Pancholi and Greg P Iacobini and Guy J. Clarkson and David W Porter and Michael Shipman},
title = {Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.7b02622},
number = {1},
pages = {491--498},
doi = {10.1021/acs.joc.7b02622}
}
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MLA
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Pancholi, Alpa K., et al. “Synthesis of 4,5-Diazaspiro[2.3]hexanes and 1,2-Diazaspiro[3.3]heptanes as Hexahydropyridazine Analogues.” Journal of Organic Chemistry, vol. 83, no. 1, Dec. 2017, pp. 491-498. https://doi.org/10.1021/acs.joc.7b02622.