Sadao Ohki

Synthesis of Nitrogen-containing Heterocyclic Compounds through Nitrilium Salt. II. Reaction of Nitriles with 2-(2-Hydroxycyclohexyl) ethanol and 1-(2-Hydroxycyclohexyl) propan-2-ol in the Presence of Acid

Reaction of 2-(2-hydroxycyclohexyl)- and 2-(2-hydroxycyclopentyl)-ethanols (VI and XX) with nitrile in the presence of stannic chloride afforded 4, 4-pentamethylene- and tetramethylene-1, 3-oxazine (VIII, XIX, and XXI). The same reaction of α-(2-hydroxycyclopentyl)-t-butanol (II) with a nitrile gave cyclopentenodihydropyridine (III). Reaction of 1-(2-hydroxycyclohexyl) propan-2-ol (XXV) and a nitrile in the presence of sulfuric acid gave 1, 3-oxazine derivative (XXVI) and cyclohexanopyrroline (XXVII) which easily underwent oxidation to a 3-hydroxy compound (XXXI).