Linked Life Data

16710863

Source:http://linkedlifedata.com/resource/pubmed/id/16710863

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
22
pubmed:dateCreated
2006-8-23
pubmed:abstractText
The reaction of o-alkynylbenzaldehydes 1 with different alcohols, silylated nucleophiles 5, electron-rich arenes 10, and heteroarenes 12 in the presence of the reagent IPy(2)BF(4), at room temperature, gave functionalized 4-iodo-1H-isochromenes 2, 6, 11, and 13 in a regioselective manner. When alkynes 16 and alkenes 19 and 20 were used as nucleophiles, a regioselective benzannulation reaction took place to form 1-iodonaphthalenes 17 and 1-naphthyl ketones 18, respectively. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives (23, 27, and 28, respectively). The three patterns of reactivity observed for the o-alkynylbenzaldehyde derivatives with IPy(2)BF(4) stem from a common iodinated isobenzopyrylium ion intermediate, A, that evolves in a different way depending on the nucleophile present in the reaction medium. A mechanism is proposed and the different reaction pathways observed as a function of the type of nucleophile are discussed. Furthermore, the reaction of the o-hexynylbenzaldehyde 1 b with styrene was monitored by NMR spectroscopy. Compound III, a resting state for the common intermediate in the absence of acid, has been isolated. Its evolution in acid media has been also tested, thereby providing support to the proposed mechanism.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
http://linkedlifedata.com/resource/pubmed/chemical/Aldehydes, http://linkedlifedata.com/resource/pubmed/chemical/Alkynes, http://linkedlifedata.com/resource/pubmed/chemical/Benzofurans, http://linkedlifedata.com/resource/pubmed/chemical/Benzopyrans, http://linkedlifedata.com/resource/pubmed/chemical/Heterocyclic Compounds, http://linkedlifedata.com/resource/pubmed/chemical/Indoles, http://linkedlifedata.com/resource/pubmed/chemical/Ions, http://linkedlifedata.com/resource/pubmed/chemical/Naphthalenes, http://linkedlifedata.com/resource/pubmed/chemical/Onium Compounds, http://linkedlifedata.com/resource/pubmed/chemical/Pyridines, http://linkedlifedata.com/resource/pubmed/chemical/Thiophenes, http://linkedlifedata.com/resource/pubmed/chemical/benzofuran, http://linkedlifedata.com/resource/pubmed/chemical/benzothiophene, http://linkedlifedata.com/resource/pubmed/chemical/bis(pyridine)iodonium(I)..., http://linkedlifedata.com/resource/pubmed/chemical/indole, http://linkedlifedata.com/resource/pubmed/chemical/naphthalene
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
0947-6539
pubmed:author
pubmed:issnType
Print
pubmed:day
24
pubmed:volume
12
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
5790-805
pubmed:dateRevised
2009-8-4
pubmed:meshHeading
pubmed:year
2006
pubmed:articleTitle
The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: a versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds.
pubmed:affiliation
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain. barluenga@uniovi.es
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't