14602-03-0Relevant articles and documents
Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group
Bode, Bela E.,Chabbra, Sonia,Champion, Sue,Dawson, Daniel M.,Sood, D. Eilidh,Sutherland, Andrew,Watson, Allan J. B.
supporting information, p. 8460 - 8463 (2020/04/10)
Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.
Four-component, five-centered, one-pot synthesis of 1-(1H-tetrazol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole derivatives
Reddy, B.V. Subba,Kota, Kavya,Rao, B. Maheshwar,Sridhar,Mukkanti
supporting information, p. 4529 - 4532 (2016/09/23)
An efficient four component, five centered coupling strategy has been developed for the synthesis of a novel series of 1-tetrazolyl-tetrahydro-β-carboline derivatives in good yields. This method is effective for the synthesis of tetrazolyl tetrahydro-β-carbolines in a one-pot operation. This method is operationally simple and works under mild conditions with diverse substrates.
Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations - New Method for the Synthesis of Pyrroloindolines
DiPoto, Maria C.,Hughes, Russell P.,Wu, Jimmy
supporting information, p. 14861 - 14864 (2015/12/08)
Herein, we report the first examples of the synthesis of pyrroloindolines by means of (3 + 2) dearomative annulation reactions between 3-substituted indoles and highly reactive azaoxyallyl cations. Computational studies using density functional theory (DFT) (B3LYP-D3/6-311G++) support a stepwise reaction pathway in which initial C-C bond formation takes place at C3 of indole, followed by ring closure to give the observed products. Insights gleaned from these calculations indicate that the solvent, either TFE or HFIP, can stabilize the transition state through H-bonding interactions with oxygen of the azaoxyallyl cation and other relevant intermediates, thereby increasing the rates of these reactions.
A short and highly convergent approach for the synthesis of rutaecarpine derivatives
Subba Reddy,Anji Babu,Jagan Mohan Reddy,Sridhar,Ramalinga Murthy,Pranathi,Kalivendi, Shasi V.,Prabhakar Rao
, p. 27476 - 27480 (2015/03/30)
A novel and highly convergent approach has been developed for the synthesis of quinazolinocarboline alkaloid, rutaecarpine, analogues by the condensation of anthranilamide with chloroaldehyde derived from tryptophol. This method also provides direct access to benzimidazocarbolines and quinazolinoisoquinolines. It is a shorter and metal-free approach which does not require any catalyst or additive to facilitate the reaction.
Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade
Han, Long,Liu, Chuan,Zhang, Wei,Shi, Xiao-Xin,You, Shu-Li
supporting information, p. 1231 - 1233 (2014/02/14)
An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.
A versatile synthetic methodology for the synthesis of tryptophols
Garden, Simon J,Da Silva, Rosangela B,Pinto, Angelo C
, p. 8399 - 8412 (2007/10/03)
Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol.
Synthesis of Novel HMG-CoA Reductase Inhibitors, II. Heterocyclic Analogs of Mevinolin
Novak, Lajos,Hornyanszky, Gabor,Rohaly, Janos,Kolonits, Pal,Szantay, Csaba
, p. 1877 - 1884 (2007/10/03)
The indole (1) and chroman analogs (2) of mevinolin and their 6S diastereomers 15c and 25d were synthesized in several steps starting with methyl (R)-3--4-formylbutyrate (12) and 2-(indol-3-yl)ethanol (3) or 6-methoxychroman-4-one (16), respectively.Compounds 1 and 2 inhibited moderately the HMG-CoA reductase.The diastereomers 15c and 25d were shown to be inactive. - Keywords: HMG-CoA reductase inhibitors / 3-Indolylheptanoates and -acetates / 4-Chromanylheptanoates and -acetates
