110128-40-0Relevant academic research and scientific papers
Wittig Olefination to New Donor and Acceptor Substituted 3-Vinylindoles: Optimized Synthetic Methods
Pindur, Ulf,Pfeuffer, Ludwig
, p. 157 - 162 (1989)
The optimized Wittig reaction of selectively functionalized 3-acylindoles yield new, and for Diels-Alder reactions highly reactive donor- and acceptor substituted 3-vinylindoles, respectively. - Keywords: 3-Vinylindoles; Donor-, acceptor substituted; Sele
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.
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.
