924906-80-9Relevant academic research and scientific papers
Intercepting the Banert cascade with nucleophilic fluorine: Direct access to α-fluorinated: N H-1,2,3-triazoles
Alexander,Kevorkian,Topczewski
supporting information, p. 5024 - 5027 (2021/05/28)
The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reacti
Squaramide catalyzed enantioselective iodolactonization of allenoic acids
Kristianslund, Renate,Aursnes, Marius,Tungen, J?rn Eivind,Hansen, Trond Vidar
supporting information, p. 5232 - 5236 (2016/11/13)
An asymmetric iodolactonization reaction of allenoic acids has been extensively studied. Eight different chiral squaramides were prepared in a straightforward manner and investigated as organocatalysts. The reaction protocol is operationally simple to exe
Selectivity in Garratt-Braverman cyclization of aryl-/heteroaryl- substituted unsymmetrical bis-propargyl systems: Formal synthesis of 7′-desmethylkealiiquinone
Das, Joyee,Mukherjee, Raja,Basak, Amit
, p. 3789 - 3798 (2014/05/20)
Unsymmetrical bis-propargyl ethers and sulfonamides containing various combinations of aryl/heteroaryl substituents at the acetylene termini were synthesized, and their reactivity under basic conditions was studied. Moderate to high (chemo)selectivity was
Domino alkylation-cyclization reaction of propargyl bromides with thioureas/thiopyrimidinones: A new facile synthesis of 2-aminothiazoles and 5H-thiazolo[3,2-α]pyrimidin-5-ones
Castagnolo, Daniele,Pagano, Mafalda,Bernardini, Martina,Botta, Maurizio
scheme or table, p. 2093 - 2096 (2011/04/15)
A new synthesis of 2-aminothiazoles and 5H-thiazolo[ 3,2-α]pyrimidin- 5-ones was developed as a domino alkylation-cyclization reaction of propargyl bromides with thioureas and thiopyrimidinones, respectively. Domino reactions were performed under microwave irradiation leading to desired compounds in a few minutes and high yields. Georg Thieme Verlag Stuttgart.
Rhodium(I)-catalyzed allenic carbocyclization reaction affording δ- and ε-lactams
Brummond, Kay M.,Painter, Thomas O.,Probst, Donald A.,Mitasev, Branko
, p. 347 - 349 (2007/10/03)
(Chemical Equation Presented) This letter extends the scope of the rhodium(I)-catalyzed allenic Alder-ene carbocyclization reaction to the preparation of δ- and ε-lactams from amides. A variety of allenic propiolamides were cycloisomerized to give a numbe
Regio- and diastereoselective allenylation of aldehydes in aqueous media: Total synthesis of (+)-goniofufurone
Yi, Xiang-Hui,Meng, Yue,Hua, Xiao-Gang,Li, Chao-Jun
, p. 7472 - 7480 (2007/10/03)
The regio- and diastereoselectivities of metal-mediated allenylation of carbonyl compounds were investigated in aqueous media. Different metal mediators showed varied regioselectivities on product formation during propargylation-allenylation reactions of carbonyl compounds with simple propargyl bromide. Under the standard reaction conditions, the use of indium provided the highest regioselectivity, with a preference of formation of the homopropargyl alcohol. The use of tin and bismuth as the metal mediator provided slightly lower selectivities with the same preference. The use of zinc and cadmium as the mediators further lowered the product selectivity. The reactions of an alipathic aldehyde with simple propargyl bromide showed a lower selectivity than the reaction of an aromatic aldehyde in most cases, except for the use of tin or zinc (where comparable selectivities were observed). On the other hand, the reaction of terminal-substituted propargyl bromides with aldehydes mediated by indium showed a high regioselectivity in forming allenylation products. The indium-mediated allenylation of carbonyl compounds bearing an α-hydroxyl group also proceeded with a high diastereoselectivity, forming syn-diols predominantly in aqueous ethanol. The high diastereoselectivity in allenylation of α-hydroxyl-substituted aldehydes was attributed to the chelation effect exhibited by the α-hydroxyl substituent. Through the use of this highly diastereoselective allenylation, (+)-goniofufurone was synthesized from D'-glucurono-6,3-lactone.
