82980-12-9Relevant academic research and scientific papers
Versus Cycloadditions with 1-Ethoxyethene and Heterocyclic Aldehydes; Formation of Vinyl Compounds
Merour, Jean-Yves,Bourlot, Anne-Sophie,Desarbre, Eric
, p. 3527 - 3530 (1995)
Inverse electron demand Diels-Alder reactions of ethoxyethene with heterocyclic aldehydes afforded a mixture of cycloadducts and vinyl compounds resulting from a competing pathway.
Borocyclopropanation of Styrenes Mediated by UV-light Under Continuous Flow Conditions
Sayes, Morgane,Benoit, Guillaume,Charette, André B.
supporting information, p. 13514 - 13518 (2018/09/25)
Herein, we report a user-friendly and metal-free UV-A light mediated borocyclopropanation of styrenes using continuous flow technology. A broad range of styrene derivatives can be cyclopropanated in good yields within 1 h residence time to produce highly
Synthesis of vinylindoles and vinylpyrroles by the Peterson olefination or by use of the Nysted reagent
Noland, Wayland E.,Etienne, Christopher L.,Lanzatella, Nicholas P.
experimental part, p. 381 - 388 (2011/05/14)
Vinylindoles and vinylpyrroles were prepared from their corresponding aldehydes or ketones using the Peterson olefination, or by use of the Nysted reagent, a commercially available gem-dimetallic compound. The two methods provide efficient and convenient
Efficient one-pot synthesis of anti-HIV and anti-tumour β-carbolines
Kusurkar, Radhika S.,Goswami, Shailesh K.
, p. 5315 - 5318 (2007/10/03)
Thermal electrocyclisation of the azahexatriene system has been used as a key step for the synthesis of anti-HIV and anti-tumour compounds, harman, derivatives of harman and 1-aryl-β-carbolines. A one-pot reaction sequence was used to furnish these compounds in good yield.
Efficient one-pot synthesis of anti HIV and antitumor compounds: Harman and substituted harmans
Kusurkar, Radhika S.,Goswami, Shailesh K.,Vyas, Sandhya M.
, p. 4761 - 4763 (2007/10/03)
Anti HIV and antitumor compounds, harman and substituted harmans have been synthesized using electrocyclization reactions as key steps. A one-pot reaction sequence was used to furnish these compounds in good overall yield.
Synthesis of novel proline and γ-lactam derivatives as non-peptide mimics of Somatostatin/Sandostatin
Damour, Dominique,Herman, Frederic,Labaudiniere, Richard,Pantel, Guy,Vuilhorgne, Marc,Mignani, Serge
, p. 10135 - 10154 (2007/10/03)
Original proline or γ-lactam derivatives bearing either an aryl group such as a phenyl or a 3-indolyl in position 3 of the proline moiety or on the 3-methyl chain of the γ-lactam skeleton were prepared as non-peptide mimics of Somatostatin/Sandostatin.
cis- and trans-3-(3-indolyl)proline derivatives as conformationally restricted analogues of tryptophan
Damour,Pulicani,Vuilhorgne,Mignani
, p. 786 - 788 (2007/10/03)
A method for the diastereoselective generation of 3-indolyl-3-proline derivatives has been developed. The [3+2] cycloaddition reaction of 3- vinylindoles with dimethyl N-ethoxycarbonyl-N-methoxymethylaminomalonate in the presence of TiCl4, afforded the title compounds after acid hydrolysis and decarboxylation reactions. These new amino acids may be viewed as conformationally restricted mimetics of tryptophan.
Sensitized photooxygenations of 3-vinylindole derivatives
Zhang,Khan,Foote
, p. 7839 - 7847 (2007/10/02)
A series of 1-methyl- and 1-(phenylsulfonyl)-substituted 3-vinylindoles with different electronic and steric features has been synthesized and their sensitized photooxygenation in aprotic solvents investigated. 1-Methyl-3- vinyl-(1a), 1,2-dimethyl-3-vinyl- (1b), 1-methyl-3-(β-methoxyvinyl)- (4-Z and 4-E), 1-(phenylsulfonyl)-3-vinyl- (8a), 1-(phenylsulfonyl)-3-(α- methylvinyl) (8b), 1-(phenylsulfonyl)-3-(β-methoxyvinyl)- (8c and 8d), and cis-1-(phenylsulfonyl)-3-(α-methyl-β-methoxyvinyl) indoles (15-Z) react with 1O2 predominantly to give endoperoxides via [4 + 2] cycloadditon. However, 1,2-dimethyl-3-(β-methoxyvinyl)indole (1c) gives [2 + 2] cycloaddition with the 3-double bond to give 1,2-dimethyl-3-formylindole (3c); trans-1-(phenylsulfonyl)-3-(α-methyl-β-methoxyvinyl)indole (15-E) gives the 3-indolyl allylic hydroperoxide (17) via ene reaction, along with a small amount of isomerization of the 3-vinyl double bond. A zwitterionic intermediate in the isomerization is proposed. Most of the resulting dioxacarbazole endoperoxides are isolable and inert to reduction by trimethyl phosphite and thiourea except for N-methyldioxacarbazole 5, which undergoes clean rearrangement to indolin-2-one epoxide 7 at -20 °C.
Palladium-catalyzed coupling of 3-indolyl triflate. Syntheses of 3-vinyl and 3-alkynylindoles
Gribble,Conway
, p. 2129 - 2141 (2007/10/02)
Palladium-catalyzed coupling of 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkynes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).
