The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Furfuryl- and thenylalkylamines from Schiff bases》. Authors are Emling, Bertin L.; Beatty, J. E.; Stevens, J. R..The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).COA of Formula: C7H8O2. Through the article, more information about this compound (cas:3194-15-8) is conveyed.
Furfural (96 g.), added dropwise to 88 g. BuNH2 at 15-20°, stirred 30 min. at room temperature, saturated with solid NaOH, and extracted with ether, gives 90% N-furfurylidenebutylamine (I), b13 90°, n20D 1.5057, d204 0.950 (all n and d. at 20°); the following homologs were prepared similarly: Me b16 53°, n 1.5269, d. 1.025, 85%; Et b18 67°, n 1.5170, d. 0.988, 86%; Pr b21 87-8°, n 1.5105, d. 0.967; Am b10 104-5°, n 1.5024, d. 0.940. N-Thenylidenebutylamine b13 112-13°, n25D 1.5459, d254 0.990. I (68 g.) in 70 ml. ether, added to EtMgBr (54.5 g. EtBr) and refluxed 2 hrs., gives 60% N-butyl-α-ethylfurfurylamine (II), b25 108-9°, n 1.4635, d. 0.907 (1-naphthylurea m. 76-7°); N-amyl-α-methylfurfurylamine b15 102-3°, n 1.4681, d. 0.913, 36% (1-naphthylurea m. 76-7°); N-propyl-α-propylfurfurylamine b24 107-8°, n 1.4634, d. 0.904, 47% (1-naphthylurea m. 87°); N-ethyl-α-butylfurfurylamine b23 105.5-6.5°, n 1.4636, d. 0.909, 47% (1-naphthylurea m. 119-19.5°); N-methyl-α-amyl-furfurylamine b3 75-6°, n 1.4649, d. 0.913, 52% (1-naphthylurea m. 121°); α-isoamyl isomer b4 67.5-8.5°, n 1.4644, d. 0.913, 55% (1-naphthylurea m. 149°). N-Butyl-α-ethylthenylamine b3 84°, n25D 1.5172, d254 0.961, 60%. Furan and (EtCO)2O with ZnCl2 give 52% furyl Et ketone; 32 g. of the oxime (68%) on reduction with Na in EtOH gives 10 g. α-ethylfurfurylamine, which with BuI in com. xylene (refluxed 4 hrs.) gives II.
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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem