100200-86-0Relevant academic research and scientific papers
Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: Access to fused pyrroles
Shi, Yi,Gevorgyan, Vladimir
, p. 5394 - 5396 (2013)
An intramolecular Rh-catalyzed transannulation reaction of alkynyl triazoles has been developed. This method allows efficient construction of various 5,5-fused pyrroles, including tetrahydropyrrolo and spiro systems. The method demonstrates excellent functional group compatibility. A rhodium carbene-alkyne metathesis mechanism is proposed for this transformation.
Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
Smith, Philip J.,Jiang, Yubo,Tong, Zixuan,Pickford, Helena D.,Christensen, Kirsten E.,Nugent, Jeremy,Anderson, Edward A.
supporting information, p. 6547 - 6552 (2021/08/30)
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.
Cobalt-catalyzed intramolecular [2 + 2 + 2] cocyclotrimerization of nitrilediynes: An efficient route to tetra- And pentacyclic pyridine derivatives
Chang, Hong-Tai,Jeganmohan, Masilamani,Cheng, Chien-Hong
, p. 505 - 508 (2007/10/03)
In this paper, we wish to report the intramolecular [2 + 2 + 2] cocyclotrimerization of nitrilediynes catalyzed by the Col2(dppe)/Zn system at 80°C in CH3CN. Under these reaction conditions, various highly substituted nitrilediynes h
Synthesis of 2-aryl-5-styrylphospholes: Promising candidates for the phosphole-based NLO chromophores
Matano, Yoshihiro,Miyajima, Tooru,Imahori, Hiroshi,Kimura, Yoshifumi
, p. 6200 - 6205 (2008/02/09)
(Chemical Equation Presented) 2-Aryl-1-phenyl-5-styrylphospholes were prepared in good yields in a one-pot procedure from the corresponding 1,9-diarylnona-8-ene-1,6-diynes and dichloro(phenyl)phosphine via intermediary titana-cyclopentadienes. According t
A convenient method for the synthesis of 2,5-difunctionalized phospholes bearing ester groups
Matano, Yoshihiro,Miyajima, Tooru,Nakabuchi, Takashi,Matsutani, Yuichiro,Imahori, Hiroshi
, p. 5792 - 5795 (2007/10/03)
Symmetrically and unsymmetrically 2,5-difunctionalized phospholes bearing ester groups were prepared in a one-pot procedure from the corresponding diynes and dichloro(phenyl)phosphine via titanacyclopentadienes. The observed optical properties of the func
AuBr3- and Cu(OTf)2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: A new synthetic method for functionalized polycyclic hydrocarbons
Asao, Naoki,Sato, Kenichiro,Menggenbateer,Yamamoto, Yoshinori
, p. 3682 - 3685 (2007/10/03)
(Chemical Equation Presented) Treatment of tethered alkynyl enynones 8, in which a carbon chain is attached to the carbonyl group, with a catalytic amount of AuBr3in (ClCH2)2 gave the naphthyl ketones 9 in good to high yields (top-down approach). Analogously, the AuBr 3-catalyzed benzannulations of 10, in which a carbon tether is extended from the alkynyl terminus, also proceeded smoothly, and the cyclized naphthyl ketones 11 were obtained in high yields (bottom-up approach). Similarly, when two kinds of tethered alkenyl enynones 12 and 14 were treated with Cu(OTf)2 catalyst, the corresponding dihydronaphthyl ketone products 13 and 15 were obtained in high yields, respectively. The present formal [4 + 2] intramolecular cycloaddition proceeds most probably through the coordination of the triple bond at the ortho position of substrates to Lewis acids, the formation of benzopyrylium ate complex 16 via the nucleophilic addition of the carbonyl oxygen atom, the reverse electron demand type Diels-Alder addition of the tethered alkynes or alkenes to the ate complex, and subsequent bond rearrangement.
From nonconjugated diynes to conjugated polyenes: Syntheses of poly(1-phenyl-7-aryl-1,6-heptadiyne)s by cyclopolymerizations of asymmetrically α,ω-disubstituted alkadiynes
Law, Charles C.W.,Lam, Jacky W.Y.,Dong, Yuping,Tong, Hui,Tang, Ben Zhong
, p. 660 - 662 (2007/10/03)
The synthesis of Poly(1-phenyl-7-aryl-1, 6-heptadiyne) by Cyclopolymerizations of asymmetrically α, ω distributed alkadiynes was discussed. The alkadiynes were prepared by a synthetic route involving consecutive palladium-catalyzed cross coupling reactions. Substitution of the olefinic hydrogen in cyclic polyene by an aromatic ring was used for the polymer stability. It was found that the polymer stability increases with a decrease in the number of the active hydrogen atoms.
