17642-88-5Relevant academic research and scientific papers
Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide
Tan, Wei,Wang, Cuihong,Jiang, Xuefeng
supporting information, p. 1234 - 1238 (2019/11/21)
We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.
Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions
Mateo, Pierre,Cinqualbre, Joséphine E.,Meyer Mojzes, Melinda,Schenk, Kurt,Renaud, Philippe
, p. 12318 - 12327 (2017/12/08)
A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.
Synthesis, spectral, and anti-microbial studies of thioiminium iodides and amine hydrochlorides
Britto, Sebastian,Renaud, Philippe,Nallu, Maruthai
supporting information, p. 489 - 493 (2013/12/04)
To avoid the undesired deprotonation during the addition of organolithium and organomagnesium reagents to ketones, the thioiminium salts, easily prepared from lactams and amides are converted into 2,2-disubstituted and 2-monosubstituted amines by reaction with simple nucleophiles such as organocerium and organocopper reagents. The reaction of thioiminium iodides with organocerium reagents derived by transmetalation of corresponding lithium reagents with anhydrous cerium(III) chloride has been investigated. These thioiminium iodides act as good electrophiles and accept alkylceriums towards bisaddition. The newly synthesized amines have been characterized by 1H and 13C NMR, IR and mass spectra. The amines have been converted into their hydrochlorides and characterized by COSY. These hydrochlorides have been subjected to antimicrobial screening with clinically isolated microorganisms, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhi and Candida albicans. The hydrochlorides show quite good activity against these bacteria and fungus.
Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids
Neto, Brenno A.D.,Lapis, Alexandre A.M.,Bernd, Alinne B.,Russowsky, Dennis
experimental part, p. 2484 - 2496 (2009/08/07)
The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.
An efficient method to convert lactams and amides into 2,2-dialkylated amines
Agosti, Alessandro,Britto, Sebastian,Renaud, Philippe
supporting information; experimental part, p. 1417 - 1420 (2009/04/12)
(Chemical Equation Presented) A practical method for the synthesis of gem-2,2-disubstituted tertiary amines from the corresponding lactams (or amides) is reported. It is based on the reaction of thioiminium ions, easily prepared from lactams and amides wi
Synthesis of ω-aminodithioesters
Lacroix, Simon,Rixhon, Vinciane,Marchand-Brynaert, Jacqueline
, p. 2327 - 2334 (2008/02/03)
ω-Aminodithioester derivatives were obtained from thionolactams by reaction with an alkyl triflate followed by thiolysis with hydrogen sulfide. The presence of an electron-withdrawing group was required on the N1 position (p-nitrophenyl or benzoyl) to favor the ring opening of γ-, δ- and ε-thionolactams. In the case of β-thionolactam, activation was provided by a CF2 motif in C3 position. Georg Thieme Verlag Stuttgart.
SYNTHESIS, STRUCTURE, AND CHEMICAL PROPERTIES OF TRIMETHYLSILYL DERIVATIVES OF THIOLACTAMS
Sergeev, V. N.,Artamkin, S. A.,Pestunovich, S. V.,Albanov, A. I.,Voronkov, M. G.,Baukov, Yu. I.
, p. 1490 - 1497 (2007/10/02)
Trimethylsilyl derivatives of five-, six-, and seven-membered thiolactams with an N-silyl structure were synthesized for the first time.Their alkylation with primary alkyl halides under comparatively mild conditions occurs at the sulfur atom; the reaction with secondary alkyl halides is accompanied by hydrogen halide elimination, and this becomes the only reaction pathway with tertiary halides.The preparative acylation of N-trimethylsilylthiolactams yields N-acyl derivatives; the intermediate formation of S-acylation products was established by means of low-temperature NMR monitoring.
In Situ Reagent for Thionation of Amides, Peptides and Lactams
Brillon, Denis
, p. 3085 - 3095 (2007/10/02)
An in situ reagent 1A for thionation of amides, peptides and lactams is prepared from phosphorus decasulfide/sodium carbonate (1:1 ratio) in THF at 25 deg C.
