Iodine-mediated new strategy for the synthesis of 2,5-disubstituted oxazoles from methyl ketones and TosMIC

Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)

“…Over the past decades, [3 + 2] cycloaddition of TosMIC with polarized functionalities, such as aldehydes, imines, alkenes, and alkynes, have been extensively explored to access five-membered heterocycles . Meanwhile, TosMIC also served as the promising C1, N1, and C1N1 building block. Recently, utilization of TosMIC as sulfinyl and sulfonyl sources has also been reported.…”

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

“…TosMIC was used as an ammonium surrogate in contrast to its typical reactivity as a C-N C synthon in the production of oxazoles 114 (Scheme 73). 93 The technique is appealing due to its ease of operation, the wide availability of 94 An insight into the mechanism initially revealed the formation of the Nacyliminium ion (NAI) precursor ua from 1 and 2-pyrrolodinone 115 under acid catalysis. There were two probable cyclization routes.…”

“…TosMIC was used as an ammonium surrogate in contrast to its typical reactivity as a C–N C synthon in the production of oxazoles 114 (Scheme 73). 93 The technique is appealing due to its ease of operation, the wide availability of the starting materials, absence of bases and metals, and the production of C–N and C–O bonds with excellent yields.…”

TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles

“…The residue was purified by silica gel column chromatography with PE/EtOAc to obtain the final product. 17 Yellow solid; yield: 97.2 mg (78%); mp 133-135 °C. 1 H NMR (600 MHz, CDCl 3 ):  = 8.48 (d, J = 7.1 Hz, 2 H), 7.87-7.82 (m, 2 H), 7.65 (t, J = 7.4 Hz, 1 H), 7.62 (s, 1 H), 7.54 (t, J = 7.8 Hz, 2 H), 7.49 (t, J = 7.5 Hz, 2 H), 7.43 (t, J = 7.4 Hz, 1 H).…”

“…Fluorophenyl)(5-(4-fluorophenyl)oxazol-2-yl)methanone (2b)17 White solid; yield: 121.2 mg (85%); mp 153-157 °C.1 H NMR (600 MHz, CDCl 3 ):  = 8.59 (d, J = 5.7 Hz, 2 H), 7.82 (d, J = 5.3 Hz, 2 H), 7.55 (s, 1 H), 7.19 (dt, J = 16.5, 8.5 Hz, 4 H). 13 C NMR (151 MHz, CDCl 3 ):  = 176.81, 166.35 (d, 1 J C,F = 256.7 Hz), 164.69 (d, 1 J C,F = 252.2 Hz), 156.85, 153.45, 133.65 (d, 3 J C,F = 10.6 Hz), 131.59 (d, 4 J C,F , J = 3.0 Hz), 127.5 (d, 3 J C,F = 9.1 Hz), 123.50, 123.02 (d, 4 J C,F = 3.0 Hz), 116.43 (d, 2 J C,F = 21.1 Hz), 115.69 (d, 2 J C,F = 21.1 Hz).…”