A novel, convenient and efficient three-component reaction for synthesizing substituted pyrroles from primary amines and electron deficient acetylenic compounds in the presence of ammonium thiocyanate in water leads to the formation of pyrroles in good yields.

The enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone has been achieved without using any protecting groups. The synthesis involved using an asymmetric alkynylation to obtain gamma-hydroxy-alpha,beta-acetylenic esters with high ee (84%) and yields ( approximately 80%), followed by selective hydrogenation and lactonization in high overall yields (87% and 89%).

A high yielding metal-catalysed Conia-ene reaction of 2-acetylenic ketones for the synthesis of bicyclo[3.n.1]alkenes has been developed. This simple and efficient 6-endo-dig-cyclization protocol enables the synthesis of a wide variety of bicyclic systems, present in many natural products.

The rearrangement of 1-ethynyl-2-propenyl pivaloates to cyclopentenones catalyzed by cationic triphenylphosphinegold(I) complexes is described. The reaction tolerates both alkyl and aryl substitution at the acetylenic and olefinic positions. Importantly, the gold(I)-catalyzed rearrangement of enantioenriched propargyl pivaloates proceeds with excellent chirality transfer, thus providing a pract...

Intramolecular inverse electron demand cycloadditions of isatin-derived 1,2,4-triazines with acetylenic dienophiles tethered by amidations or transesterifications proceed in excellent yields to produce lactam- or lactone-fused α-carbolines. Beginning with various isatins and alkynyl dienophiles, a pilot-scale library of eighty-eight α-carbolines was prepared by using this robust methodology for...

Type III-B first generation [3]rotaxane and second generation [4]rotaxane dendrimers have been synthesized via (1) a modified copper-catalyzed alkyne-azide cycloaddition (CuAAC), (2) Glaser-Hay's acetylenic oxidative homo-coupling, and (3) amide formation. The dendron does not reveal obvious cytotoxicities in L929 fibroblast cells. The rotaxane dendrimers can capture ammonia and are switchable ...

Optimization study of the diesters biolubricant oleyl 9(12)-hydroxy-10(13)-oleioxy-12(9)-octadecanoate (OLHYOOT) was synthesized in the presence of sulfuric acid (SA) as catalyst has been done. Optimum conditions of the experiment to obtain high yield% of OLHYOOT were predicted at ratio of OL/HYOOA of 1:1 g/g, ratio of SA/HYOOA of 0.20:1 g/g, reaction temperature 110 °C and 4.5 h of reaction ti...

Cationic tri-tert-butylphosphinegold(I) serves as a catalyst in the sila-Cope rearrangement of acetylenic allylsilanes. When phenol is employed as a nucleophile, the reaction allows for the stereoselective synthesis of vinylsilanes. Alternatively, use of methanol as a nucleophile leads to cyclic vinylsilanes, which can be viewed as latent vinylsilanes that are revealed on treatment with a mild ...

New acetylenic nematicidal compound, penipratynolene (1), methy (2'R)-4-(2'-hydroxy-3'-butynoxy)benzoate, together with two known compounds, 6-methoxycarbonylpicolinic acid (2) and 2,6-pyridinedicarboxylic acid (3), were isolated from the culture filtrate of Penicillium bilaiae Chalabuda. The structures of 1-3 were established by spectroscopic methods. The absolute configuration of 1 was confir...