Regioselective synthesis of C3 alkylated and arylated benzothiophenes was written by Shrives, Harry J.;Fernandez-Salas, Jose A.;Hedtke, Christin;Pulis, Alexander P.;Procter, David J.. And the article was included in Nature Communications in 2017.Synthetic Route of C11H15NO2 This article mentions the following:
The method for completely regioselective, metal-free C3 C-H functionalization of benzothiophenes e.g., I that utilizes synthetically unexplored benzothiophene S-oxides II (R1 = H, 5-NO2, 6-Br, etc.; R2 = H, CO2CH3, CN, etc.), readily available from straightforward oxidation of benzothiophenes such as 5-bromobenzo[b]thiophene, 2-phenylbenzo[b]thiophene, 2-methylbenzo[b]thiophene, etc. and phenols such as p-cresol, 4-iodophenol, 4-nitrophenol, etc./propargyl silanes such as trimethyl(allyl)silane, trimethyl(2-bromoallyl)silane, 2-((trimethylsilyl)methyl)allyl acetate, etc. and allyl silanes such as propargyl silane, hex-1-yne-1,3-diylbis(trimethylsilane), hept-2-yn-1-yltrimethylsilane, etc. was described. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Synthetic Route of C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics