139416-74-3Relevant academic research and scientific papers
Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives
Mancuso, Raffaella,Miliè, Rossana,Palumbo Piccionello, Antonio,Olivieri, Diego,Della Ca, Nicola,Carfagna, Carla,Gabriele, Bartolo
supporting information, p. 7303 - 7311 (2019/06/17)
A catalytic carbonylative double cyclization method for the synthesis of furo[3,4-b]benzofuran-1(3H)-ones is reported. It is based on the reaction between readily available 2-(3-hydroxy-1-yn-1-yl)phenols, CO, and oxygen carried out in the presence of cata
Convenient and highly efficient routes to 2 H-chromene and 4-chromanone derivatives: Iodine-promoted and p-toluenesulfonic acid catalyzed cascade cyclizations of propynols
Qiu, Yi-Feng,Ye, Yu-Ying,Song, Xian-Rong,Zhu, Xin-Yu,Yang, Fang,Song, Bo,Wang, Jia,Hua, Hui-Liang,He, Yu-Tao,Han, Ya-Ping,Liu, Xue-Yuan,Liang, Yong-Min
supporting information, p. 3480 - 3487 (2015/03/04)
A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99%). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.
BF3·Et2O-promoted cleavage of the Csp-Csp2 bond of 2-propynolphenols/anilines: Route to C2-alkenylated benzoxazoles and benzimidazoles
Song, Xian-Rong,Qiu, Yi-Feng,Song, Bo,Hao, Xin-Hua,Han, Ya-Ping,Gao, Pin,Liu, Xue-Yuan,Liang, Yong-Min
, p. 2263 - 2271 (2015/03/18)
A novel BF3·Et2O-promoted tandem reaction of easily prepared 2-propynolphenols/anilines and trimethylsilyl azide is developed to give C2-alkenylated benzoxazoles and benzimidazoles in moderate to good yields. Most reactions could be accomplished in 30 min at room temperature. This tandem process involves a Csp-Csp2 bond cleavage and a C-N bond formation. Moreover, both tertiary and secondary propargylic alcohols with diverse functional groups were tolerated under the mild conditions.
Potassium tert-butoxide promoted annulation of 2-alkynylphenyl propargyl ethers: Selective synthesis of benzofuran and 12H-benzoannulene derivatives
Grimaldi, Tamiris B.,Back, Davi F.,Zeni, Gilson
, p. 11017 - 11031 (2013/11/19)
We present here our results on potassium tert-butoxide promoted annulation reactions of 2-alkynylphenyl propargyl ethers to give two different types of heterocycles: 3-benzyl-2-alkynylbenzofurans and 12H-benzoannulenbenzo[b]furans. A series of functionalized 2-alkynylphenyl propargyl ethers were efficiently cyclized by potassium tert-butoxide to the corresponding products. The optimized reaction conditions tolerated a large variety of functional groups, including electron-rich, electron-poor, and N-heterocyclic substrates. Selective product formation was obtained by controlling the solvent and temperature. When THF was used at room temperature, 3-benzyl-2-alkynylbenzofuran derivatives were exclusively obtained, while the use of DMF at 60 C gave selectively 12H-benzoannulen[b]benzofurans.
Pd/C mediated synthesis of 2-substituted benzo[b]furans/nitrobenzo[b] furans in water
Pal, Manojit,Subramanian, Venkataraman,Yeleswarapu, Koteswar Rao
, p. 8221 - 8225 (2007/10/03)
An efficient synthesis of 2-alkyl/aryl substituted benzo[b]furans/nitrobenzo[b]furans in water has been accomplished via Pd/C catalyzed reaction of o-iodophenols with terminal alkynes in the presence of PPh3, CuI and prolinol. This method can t
Palladium-catalysed heteroannulation with acetylenic compounds: Synthesis of benzofurans
Kundu, Nitya G.,Pal, Manojit,Mahanty, Jyan S.,De, Mahuya
, p. 2815 - 2820 (2007/10/03)
A detailed study of the heteroannulation of 0-iodophenol with acetylenic substrates through palladiumcopper catalysis leading to the synthesis of the 2-substituted benzofurans 21-29 is reported. An acylic compound 30 has been isolated and proved to be an intermediate in the synthesis of the benzofurans. Some of the benzofurans have been transformed into biologically active compounds.
Palladium-catalysed Heteroannulation of Acetylenic Compounds: a Facile Method for the Synthesis of Benzofurans
Kundu, Nitya G.,Pal, Manojit,Mahanty, Jyan S.,Dasgupta, Swapan K.
, p. 41 - 42 (2007/10/02)
A convenient and general method for the synthesis of benzofurans from o-iodophenol and acetylenic compounds under palladium-catalysed conditions is described.
Reaction of 4-Chlorocoumarin with Organometallic Reagents. Synthesis of Trialkylbenzopyrans, 4-Chlorobenzopyrans, 4-Alkylcoumarins and o-Hydroxyphenylprop-2-ynyl Alcohols
Alberola, Angel,Calvo, Blanca,Ortega, Alfonso Gonzalez,Pedrosa, Rafael
, p. 3075 - 3080 (2007/10/02)
4-Chlorocoumarin has been shown to be a highly versatile starting material when treated with organometallic reagents.Thus, it has allowed the selective synthesis either directly, or through simple additional transformations, of 4-alkylcoumarins (with R2CuLi in Et2O, or PriMgBr in THF), 2-chloro-2-(o-hydroxyphenyl)allyl alcohols or their 4-chloro-2H-1-benzopyran derivatives (with RMgX in THF), 2-(o-hydroxyphenyl)prop-2-ynyl alcohols (when non-acid hydrolysis were used in the latter reactions) and 2,2,4-trialkyl-2H-1-benzopyrans (when excess of RMgX or R3Al reagents were used).
