53877-63-7Relevant academic research and scientific papers
Phosphine-promoted cyclization of dicyclopropenones
Yang, Jin-Ming,Tang, Xiang-Ying,Wei, Yin,Shi, Min
, p. 3545 - 3552 (2013)
A novel phosphine-promoted intramolecular cyclization of dicyclopropenones 1 has been described in this contribution. A variety of 2,3-dihydro-1H-indene-4, 6-diol derivatives 2 and hexahydropentalen-2-one derivatives 3 were obtained selectively in moderat
Gold(I)-Catalyzed Cascade Cyclization of Anilines with Diynes: Controllable Formation of Eight-Membered Ring-Fused Indoles and Propellane-Type Indolines
Yamaguchi, Ayuta,Inuki, Shinsuke,Tokimizu, Yusuke,Oishi, Shinya,Ohno, Hiroaki
, p. 2543 - 2559 (2020/03/13)
Heterocycle-fused indoles or indolines are distributed widely in a variety of natural products, bioactive agents, and pharmaceuticals. Herein, we describe the development of gold-catalyzed cascade reactions of anilines with diynes to form eight-membered r
On the Distribution of Linear versus Angular Naphthalenes in Aromatic Tetradehydro-Diels–Alder Reactions – Effect of Linker Structure and Steric Bulk
Chinta, Bhavani Shankar,Baire, Beeraiah
, p. 3381 - 3385 (2017/06/29)
We report here a systematic study of the aromatic tetradehydro-Diels–Alder (Ar-TDDA) reaction to elucidate the factors that have significant effects on the distribution of linear and angular naphthalene products. Two factors were studied, that is, the nat
A Ruthenium Complex-Catalyzed Cyclotrimerization of Halodiynes with Nitriles. Synthesis of 2- and 3-Halopyridines
Bedná?ová, Eva,Colacino, Evelina,Lamaty, Frédéric,Kotora, Martin
supporting information, p. 1916 - 1923 (2016/07/06)
Monohalo- and dihalodiynes efficiently undergo [2+2+2] cyclotrimerization with nitriles in the presence of a catalytic amount of the ruthenium complex Cp*RuCl(cod) (10 mol%) to afford the corresponding halopyridines under ambient conditions in good isolated yields (up to 90%). The halopyridines are formed as two separable regioisomers. This is the first example of a direct synthesis of halopyridines from haloalkynes and nitriles. (Figure presented.) .
Synthesis of phthalides from bis-propargyl ethers: Use of Garratt-Braverman cyclization to construct the phthalans and IBX as a new reagent for subsequent oxidation
Panja, Arpita,Das, Eshani,Maji, Manasi,Basak, Amit
supporting information, p. 5986 - 5990 (2015/10/28)
An efficient route to phthalides is described starting from easily available bis-propargyl ethers. The method involves Garratt-Braverman cyclization of the ethers to phthalans which are then efficiently oxidized to the phthalides by iodoxy benzoic acid (IBX) which has been shown to be a superior reagent in terms of yield and reagent stoichiometry for such a transformation in comparison with more commonly used KMnO4/CuSO4 reagent.
Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO
Kudoh, Takayuki,Mori, Tomoko,Shirahama, Mitsuhito,Yamada, Masashi,Ishikawa, Teruhiko,Saito, Seiki,Kobayashi, Hisayoshi
, p. 4939 - 4947 (2008/02/03)
Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.
