954-54-1Relevant academic research and scientific papers
Photochemistry of thiophene-S-oxide derivatives
Heying, Melanie J.,Nag, Mrinmoy,Jenks, William S.
experimental part, p. 915 - 924 (2009/10/26)
Photolysis of substituted thiophene-S-oxides in solution results in the formation of either the corresponding thiophene or furan, in addition to uncharacterized materials. No good rationalization is available for the choice of which pathway may predominat
Synthesis and evaluation of estrogen receptor ligands with bridged oxabicyclic cores containing a diarylethylene motif: Estrogen antagonists of unusual structure
Zhou, Hai-Bing,Comninos, John S.,Stossi, Fabio,Katzenellenbogen, Benita S.,Katzenellenbogen, John A.
, p. 7261 - 7274 (2007/10/03)
A new series of ligands for the estrogen receptor (ER) based on a three-dimensional structural motif consisting of a bridged oxabicyclic core (7-oxabicyclo[2.2.1]heptene or heptadiene) were synthesized and examined for their receptor binding activity and as regulators of transcription through the two ER subtypes, ERα and ERβ. The prototypical ligands also contain a 1,2-diarylethylene motif, common to many nonsteroidal estrogens, as an embellishment on the oxabicyclic core. Thus, these ligands bear peripheral groups typically found in ER ligands, built here upon an overall three-dimensional core topology that is unusual for these targets. Most of these compounds were conveniently synthesized by a Diels-Alder reaction of various 3,4-diarylfurans with a variety of dienophiles, neat and under mild conditions in the absence of catalysts. Some of the synthesized compounds display good binding affinity for the ER, and in transcription assays, the highest affinity compounds are antagonists on both ERs. Molecular modeling studies suggest a structural basis for the antagonist activity of these compounds. These compounds, based on the bicyclo[2.2.1]core system, expand the structural diversity of ligands that can be antagonists for the estrogen receptors.
Magnesium mediated carbometallation of propargyl alcohols: Direct routes to furans and furanones
Forgione, Pat,Wilson, Peter D.,Fallis, Alex G.
, p. 17 - 20 (2007/10/03)
The addition of vinyl and aryl Grignard reagents to propargyl alcohols for the direct synthesis of furans and butenolides from a one pot reaction is described. These products arise from a putative magnesium chelate intermediate 2 upon reaction with various electrophiles. This chelate was also generated in situ from alkynyl lithium addition to aldehydes followed by magnesium exchange and Grignard addition. Thus, the complete substitution pattern for the furan ring may be controlled, as desired, through the judicious choice of substrates and reagents.
Regiospecific synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan as building blocks
Yang,Wong
, p. 9583 - 9608 (2007/10/02)
3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan have been prepared and used successfully as building blocks to lead to various 3,4-disubstituted furans and 3-substituted furans, respectively.
3,4-Bis(tributylstannyl)furan: a Versatile Building Block for the Regiospecific Synthesis of 3,4-Disubstituted Furans
Yang, Yun,Wong, Henry N. C.
, p. 656 - 658 (2007/10/02)
By utilising an oxazole-alkyne Diels-Alder reaction, 3,4-bis(tributylstannyl)furan is prepared and its synthetic potential assessed by its conversion into several 3,4-disubstituted furans via Stille-type palladium-catalysed reactions.
A New and Versatile Synthesis of Furans
Koenig, Horst,Graf, Fritz,Weberndoerfer, Volkmar
, p. 668 - 682 (2007/10/02)
The thermal reaction of oxazoles 1 and acetylenic dienophiles 2 provides a synthetic approach to a great variety of furans (Table 1).Scope and mechanism of this reaction are discussed.Biologically active substances of type 7 are described as examples for practical application.
