65102-22-9Relevant academic research and scientific papers
NOVEL COMPOUNDS
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Page/Page column 58, (2015/12/17)
Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
A sulfoxide-based ring annelation approach to fused, many-membered ring N,S-heterocycles
Bates, Dallas K.,Xia, Mingde
, p. 9190 - 9196 (2007/10/03)
An approach to many-membered ring N,S-heterocycles involving sulfoxide electrophilic sulfenylation (SES) followed by ring expansion of the derived sulfonium salt intermediate (in situ) is illustrated for 9- and 10-membered- ring compounds. Treatment of readily prepared sulfoxides 10a, 10b, 18a, 18b, 23a, and 23b with triflic anhydride (pyridine, CH2Cl2, 0 °C) provides heterocycles 13a (65%), 13b (60%), 19a (67%), 19b (67%), 24a (42%), and 24b (80%), respectively. Sulfoxides 5a and 5b, under several different conditions, give only the Pummerer dehydration products 6a and 6b, respectively. Diastereomeric sulfoxides 18a' and 18b', upon treatment with triflic anhydride, do not produce clean product mixtures or any of the desired heterocyclic products but, upon heating in toluene, are converted to the more stable isomers 18a and 18b, respectively. Conducting this isomerization in the presence of 2-mercaptobenzothiazole produces a disulfide indicative of the intermediacy of a sulfenic acid. However, the importance of sulfenic acid derivatives in the SES process leading to many-membered ring heterocycles remains to be determined.
Tandem SN2-Michael Reactions for the Preparation of Simple Five- and Six-Membered-Ring Nitrogen and Sulfur Heterocycles
Bunce, Richard A.,Peeples, Christopher J.,Jones, Paul B.
, p. 1727 - 1733 (2007/10/02)
A one-pot tandem SN2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters.Nitrogen-containing rings are prepared by reaction of the ω-halo-2-alkenoate ester with a primary amine in the presence of triethylamine.The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt.Yields are routinely in the 60-80percent range.Experiments are described which elucidate the chronology of the reaction sequences.Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.
