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. Author manuscript; available in PMC: 2017 Feb 17.
Published in final edited form as: Tetrahedron Lett. 2016 Feb 17;57(7):757–759. doi: 10.1016/j.tetlet.2016.01.016

Table 1.

Synthesis of Extended 2-Substituted Oxazoles

graphic file with name nihms752887u3.jpg
Conditions Product Yield (%)
a graphic file with name nihms752887t1.jpg 63
b graphic file with name nihms752887t2.jpg 40
c graphic file with name nihms752887t3.jpg 70
d graphic file with name nihms752887t4.jpg 81
e graphic file with name nihms752887t5.jpg 90
f graphic file with name nihms752887t6.jpg 80
g graphic file with name nihms752887t7.jpg 85
h graphic file with name nihms752887t8.jpg 96
i graphic file with name nihms752887t9.jpg 80
j graphic file with name nihms752887t10.jpg 72
k graphic file with name nihms752887t11.jpg 93
l graphic file with name nihms752887t12.jpg 90
m graphic file with name nihms752887t13.jpg 30
n graphic file with name nihms752887t14.jpg 41

Reagents and conditions: (a) ethanolamine/ethanol/reflux/6h. (b) cyclohexylamine/TEA/THF/60°C/2h. (c) aniline/85°C/12h. (d) diethylamine/benzene/reflux/3h. (e) morpholine/benzene/refux/8h. (f) N-methylpiperazine/TEA/THF/reflux/2h. (g) imidazole/NaH/DMF/5°C/2h. (h) NaOMe/MeOH/5°C to rt/16h. (i) NaOEt/EtOH/5°C to rt/16h. (j) 4-bromophenol/K2CO3/DMF/100°C. (k) KSCN/acetone/reflux/3h. (l) PhSH/NaH/DMF/5°C to rt. (m) PPh3/toluene/reflux/16h. (n) NaCN/DMF/10°C to rt/16h.