FACILE SYNTHESIS OF ISOXAZOLE 4- AND 5-CARBALDEHYDES AND THEIR CONVERSION TO ISOXAZOLYL-1, 4-DIHYDROPYRIDINES

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• The required nitro compounds were prepared by a one-pot synthesis involving successive reactions of nitromethane respectively with aldehydes, acylating agents, and sodium borohydride.11 1-Nitroheptane (70%. bp. 80–83°. ∼12–16 mmHg); IR 1550 (NO2), 1380 cm−1 1-Nitrooctane (44%, bp. 90–94°, ∼12–16 mmHg); IR 1550 (NO2), 1380, 1130 cm−1 4-Phenyl-1-Nitroheptane (30%, eluent, petroleum ether: EtOAc; 10:1, Rf = 0.28); IR 3000, 1950, 1870, 1600, 1550 (NO2), 1375 cm−1
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• Compound 6a was prepared from propargyl alcohol12 in 92% yield, (bp. 50–55°, ∼12–16 mmHg). b) Compound 6b was prepared from propargyl alcohol and benzoyl chloride in 94% yield (bp. 37–40°, ∼12–16 dg)
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• The required 3-n-alkyl-5-‘(tetrahydropyranyloxy)methyl’ isoxazole was prepared accordingly, 7a (48%); IR (neat) 3100, 1605, 1480, 1200, 1120, 1070, 1130 cm−1 7b (48%); IR (neat) 3100, 1605, 1460–1420, 1200, 1120, 1070cm−1 7c (50%); IR (neat) 3100, 1605, 1460–1420, 1200, 1120, 1070cm−1 7e (56%); IR (neat) 3105, 1605, 1480–1420, 1200, 1120, 1070cm−1 7f yellow oil (40%. eluent, petroleum ether: EtOAc; 10:1, Rf = 0.25); IR (neat) 3105, 3050, 2900–2850, 1600, 1480, 1450, 1380, 1250, 1200, 1100, 1070cm−1 b) The required 3-n-alkyl-5-‘(phenyl carboxylate)methyl’ isoxazole were prepared according to the procedure for 7d. 7g (75%, petroleum ether: EtOAc; 9:1, Rf = 0.45); IR (neat) 3110, 3050, 1725, 1600, 1250, 1110cm−1 7h (75%, petroleum ether: EtOAc, 9:1, Rf = 0.42);IR (neat) 3150, 3050, 1730, 1600, 1260, 1100 cm−1
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