4327-52-0Relevant academic research and scientific papers
A simple and efficient method for synthesis of benzothiazepine derivatives
Itabashi, Saori,Lu, Rong,Miyakoshi, Tetsuo
scheme or table, p. 171 - 177 (2011/04/26)
A series of 1, 5-benzothiazepines were synthesized using disulfides and α, β-unsaturated carbonyl or nitrile compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with α,β-unsaturated carbonyl or nitrile compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2, 2, 4-trymethyl-3H-1, 5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino- phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl) propionic acid ethyl esters (4) were produced. Subsequently, the 1, 5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction. The Japan Institute of Heterocyclic Chemistry.
Catalysis by an ionic liquid: Efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions
Ranu, Brindaban C.,Dey, Suvendu S.,Hajra, Alakananda
, p. 2417 - 2421 (2007/10/03)
An inexpensive and readily available ionic liquid, tetrabutylammonium bromide in the molten state, efficiently catalyzes the conjugate addition of thiols to α,β-unsaturated nitriles, carboxylic ester, ketones and aldehydes as well as nitro olefins.
