173276-69-2Relevant academic research and scientific papers
Coupling reactions and coupling-alkylations of thiophenecarbaldehydes promoted by samarium diiodide
Yang, Shyh-Ming,Fang, Jim-Min
, p. 394 - 399 (2007/10/03)
The coupling reactions of 2-thiophenecarbaldehyde with aromatic or aliphatic aldehydes were promoted by samarium diiodide in the presence of hexamethylphosphoramide to give C-5 hydroxyalkylation products. The coupling reactions of 3-thiophenecarbaldehyde occurred at C-2, and the subsequent alkylations occurred at the sulfur atom, accompanied by a concurrent opening of the thiophene ring to afford γ-lactols. Double hydroxyalkylations of 2- and 3-thiophenecarbaldehydes were also carried out under appropriate reaction conditions. Synthetic applications of these thiophenecarbonyl coupling products were demonstrated, for example, by elaboration to furans, butenolides, and thiophene-fused polycyclic compounds.
Samarium diiodide promoted coupling of thiophenecarbaldehydes
Yang, Shyn-Ming,Fang, Jim-Min
, p. 2669 - 2672 (2007/10/02)
Thiophene-2-carbaldehyde adds to aromatic and aliphatic aldehydes with the mediation of samarium diiodide and hexamethylphosphoramide.These hydroxyalkylations occur at the 5-position of thiophene-2-carbaldehyde.The self- and cross-coupling reactions of thiophene-3-carbaldehyde occur at the 2-position.S-Alkylation of the reaction intermediates gives substituted γ-lactols.
An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans
Kuroda, Tooru,Takahashi, Masami,Ogiku, Tsuyoshi,Ohmizu, Hiroshi,Nishitani, Takashi,et al.
, p. 7353 - 7357 (2007/10/02)
The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate.A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.
