Synthesis of furan derivatives. LXXXV. Condensation of heteroaromatic aldehydes with tosylmethyl isocyanide.

Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles

“…An oxazole ring substituted in the 5-position can be synthesized from the corresponding aldehydes using van Leusen’s reagent, tosyl methyl isocyanide (TosMIC) [38–39]. For the preparation of 5-(2-vinylstyryl)oxazole ( 2 ) by this method 3-(2-vinylphenyl)acrylaldehyde ( 6 ) was needed.…”

A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

“…5-Phenyl-oxazole (35a) [54,59] Yield [52] Yield [55] Yield 80 %; Gummy solid; FT-IR ( N, 6.98. [59] Yield Nitro-phenyl)-oxazole (35e) [52,54] Yield 68 %; Yellow solid; mp 137-139 °C; FT-IR (cm -1 ): Fluoro-phenyl)-oxazole (35f) [59] Yield 74 %; Off white solid; mp 36-38 °C; FT-IR (cm [54] Yield 72 %; Off white solid; mp 65-67 °C; FT-IR (cm -1 ): [49] Yield 70 %; Pale yellow solid; mp 77-79 °C; FT-IR ( 5-Naphthalen-1-yl-oxazole (35i) [53] Yield 5-Thiophen-2-yl-oxazole (35j) [65] Yield 69 %; Gummy; FT-IR (cm [65] Yield 61 %; Gummy; FT-IR (cm 2-Oxazol-5-yl-pyridine (35l) [65] Yield 71 %; Gummy; FT-IR (…”

p -Toluenesulfonylmethyl Isocyanide: a Versatile Synthon in Organic Chemistry

“…Alkyl-substituted TosMIC homologs 17 on reaction with benzaldehyde in the presence of K 2 CO 3 and MeOH yield 4-alkyl-5-aryl substituted oxazoles(31) [31,32] (Scheme 14).…”

“…The dianion of TosMIC is essential to act as a nucleophile during the course of its reaction with the ester carbonyl function [26] (Scheme 15). Heteroaromatic substituted oxazoles 35 were prepared using a similar method by condensation of heteroaromatic aldehydes with tosylmethyl isocyanide[32]:Various oxazoles prepared are listed inTable II. The only exception is the reaction with pyrrole-2-carbaldehyde, leading to formation of 3-tosylpyrolo[1,2-c]pyrimidine[32].…”

“…Heteroaromatic substituted oxazoles 35 were prepared using a similar method by condensation of heteroaromatic aldehydes with tosylmethyl isocyanide[32]:Various oxazoles prepared are listed inTable II. The only exception is the reaction with pyrrole-2-carbaldehyde, leading to formation of 3-tosylpyrolo[1,2-c]pyrimidine[32]. TosMIC and monosubstituted TosMIC homologs (36) react with ,-unsaturated aldehydes (37) to form oxazoles 38[33] (Scheme 16).Similarly, the monosubstituted derivative of TosMIC (39) on reaction with formaldehyde forms oxazole 40[34] (Scheme 17).…”