250586-16-4Relevant academic research and scientific papers
Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide
Yata, Tetsuji,Kita, Yuji,Nishimoto, Yoshihiro,Yasuda, Makoto
, p. 14330 - 14341 (2019)
The oxyindation of carbonyl-ene-yne compounds with indium trihalides proceeded efficiently to give di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrone and a zwitterion intermediate were identified by X-ray crystallographic analysis. The application of organoindium compounds to oxidation or cross-coupling provided easy access to various multifunctionalized 2-pyrones. Some 2-pyrone derivatives show intense fluorescence only in the solid state (aggregation-induced emission).
Palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide
Xie, Zheng,Wu, Pan,Cai, Liangzhen,Tong, Xiaofeng
supporting information, p. 2160 - 2162 (2014/04/03)
This Letter describes a palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide in the presence of alkylol, which provides a facile access to 2-alkoxy-3-methylene-tetrahydropyridine. The asymmetric version of this reaction has also been preliminarily realized with up to 81% enantioselectivity when chiral bisphosphine ligands were used.
Synthesis of 3-pyrroline via domino Heck-aza-Michael reaction
Wu, Pan,Liu, Hui,Tong, Xiaofeng
supporting information; experimental part, p. 4673 - 4675 (2012/09/05)
This Letter describes the Pd(0)-catalyzed domino Heck-aza-Michael reaction between (Z)-N-(3-iodoallyl)-tosylamide and acrylic ester. The reaction provides a facile access to an important class of substituted 3-pyrroline.
Palladium-catalyzed Heck-type reaction of oxime ether bearing a pendant vinyl iodide moiety
Liu, Hui,Wang, Limin,Tong, Xiaofeng
supporting information; experimental part, p. 12206 - 12208 (2011/12/16)
A Pd(0)-catalyzed intramolecular Heck-type reaction of oxime ether has been developed, providing convenient access to heterocyclic oximes. The Royal Society of Chemistry 2011.
General and regioselective synthesis of substituted pyrroles by metal-catalyzed or spontaneous cycloisomerization of (Z)-(2-en-4-ynyl)amines
Gabriele, Bartolo,Salerno, Giuseppe,Fazio, Alessia
, p. 7853 - 7861 (2007/10/03)
A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl)amines 1 is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group, enynamines were stable and could be converted into the corresponding pyrroles by metal catalysis. CuCl 2 was found to be an excellent catalyst for cycloisomerization of substrates substituted at C-3, while PdX2 in conjunction with KX (X = Cl, I) turned out to be a superior catalyst for the reaction of enynamines unsubstituted at C-3.
