Document Detail


Ultrasound-promoted synthesis of novel dispirocyclic frameworks from aza-Claisen rearrangements of Baylis-Hillman amines.
MedLine Citation:
PMID:  18848799     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A novel tetracyclic frameworks of dispiropyrrolizidines can be obtained in moderate to good yields via the 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles derived from aza-Claisen rearrangement of Baylis-Hillman amines. The transformations are highly regioselective and stereoselective, affording the desired compounds in reduced time and increased yields under ultrasound irradiation at room temperature. All the products are confirmed by 1H, 13C NMR, IR and MS spectra, while their molecular structures are elucidated by X-ray crystallography of a selected sample.
Authors:
Shao-Qin Ge; Yun-Yu Hua; Min Xia
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-09-11
Journal Detail:
Title:  Ultrasonics sonochemistry     Volume:  16     ISSN:  1350-4177     ISO Abbreviation:  Ultrason Sonochem     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2008-10-30     Completed Date:  2009-02-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9433356     Medline TA:  Ultrason Sonochem     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  232-6     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P.R. China.
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MeSH Terms
Descriptor/Qualifier:
Amines / chemistry*,  radiation effects*
Aza Compounds / chemistry*,  radiation effects*
Cyclization
Indicators and Reagents
Isatin / chemistry
Models, Molecular
Proline / chemistry
Pyrrolizidine Alkaloids / chemical synthesis*,  radiation effects
Spiro Compounds / chemical synthesis*,  radiation effects
Ultrasonics*
X-Ray Diffraction
Chemical
Reg. No./Substance:
0/Amines; 0/Aza Compounds; 0/Indicators and Reagents; 0/Pyrrolizidine Alkaloids; 0/Spiro Compounds; 147-85-3/Proline; 91-56-5/Isatin

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