Source:http://linkedlifedata.com/resource/pubmed/id/20572184
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
32
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pubmed:dateCreated |
2010-8-23
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pubmed:abstractText |
A procedure for the synthesis of functionalized, substituted pyrroles by 1,3-dipolar cycloaddition of azomethine ylides has been developed. This protocol is based on the metal-catalyzed cycloaddition of alpha-iminoesters with sulfonyl dipolarophiles, followed by the base-promoted elimination of the sulfonyl groups. A wide variety of 2,5-disubstituted and 2,3,5- and 2,4,5-trisubstituted pyrroles have been prepared in satisfactory yields from 1,2-bis(sulfonyl ethylene), beta-sulfonylenones, and beta-sulfonylacrylates. This method can be applied in an iterative and straightforward manner to the construction of oligopyrroles, from bipyrroles to pentapyrroles. Iterative [n+1] and [n+2] approaches have been devised, the latter involves double 1,3-dipolar cycloaddition from pyrrolyl-based bis(iminoesters).
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Azo Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Pyrroles,
http://linkedlifedata.com/resource/pubmed/chemical/Sulfones,
http://linkedlifedata.com/resource/pubmed/chemical/Thiosemicarbazones,
http://linkedlifedata.com/resource/pubmed/chemical/azomethine
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
1521-3765
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pubmed:author | |
pubmed:issnType |
Electronic
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pubmed:day |
23
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pubmed:volume |
16
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
9864-73
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pubmed:meshHeading |
pubmed-meshheading:20572184-Azo Compounds,
pubmed-meshheading:20572184-Catalysis,
pubmed-meshheading:20572184-Combinatorial Chemistry Techniques,
pubmed-meshheading:20572184-Cyclization,
pubmed-meshheading:20572184-Molecular Structure,
pubmed-meshheading:20572184-Pyrroles,
pubmed-meshheading:20572184-Sulfones,
pubmed-meshheading:20572184-Thiosemicarbazones
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pubmed:year |
2010
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pubmed:articleTitle |
Pyrrole and oligopyrrole synthesis by 1,3-dipolar cycloaddition of azomethine ylides with sulfonyl dipolarophiles.
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pubmed:affiliation |
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco 28049, Madrid, Spain.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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