Journal
TETRAHEDRON LETTERS
Volume 50, Issue 3, Pages 291-294Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.10.145
Keywords
Cycloaddition; Ring fragmentation; Heterocycles; Spirocycles; Tandem reactions; Regioselectivity
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Funding
- NCRR NIH HHS [G12 RR013459] Funding Source: Medline
- NIGMS NIH HHS [S06 GM008047-34S10050, S06 GM008047, SC3 GM094081] Funding Source: Medline
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The syntheses of an important class of hitherto unreported 1,3,5-pyrazoles, inspired by all unanticipated eliminatory ring opening are described, The reported pyrazole compounds were constructed through the Huisgen cyclization of 2-methylene-1,3,3-trimethylindoline and an in situ generated nitrile imine. The newly formed spiro-pyrazoline intermediate presumably then undergoes a ring opening/elimination process to afford a pyrazole, as evidenced by single X-ray crystal data. The Current report constitutes the first formal observation of this kind of ring opening involving a spiro-pyrazoline intermediate. Published by Elsevier Ltd.
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