Process for producing azine compounds and oxime compounds

A process for producing an oxime compound, the process comprising allowing an azine compound represented by following Formula (3):

• 32
• wherein Ra, Rb, Rc and Rd are the same or different and are each a hydrogen atom or a hydrocarbon group, and wherein Ra and Rb, Rc and Rd may be combined to form a ring together with the adjacent carbon atom, respectively, to react with water to yield oxime compounds represented by following Formulae (4a) and/or (4b):
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• wherein Ra, Rb, Rc and Rd have the same meanings as defined above, in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (A) in its ring:
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• wherein X is one of an oxygen atom and an —OR group, and wherein R is one of a hydrogen atom and a hydroxyl-protecting group.

A process for producing an azine compound or an oxime compound, the process comprising allowing at least one pair of compounds selected from three pairs of:

• a pair of compounds each having a methylene group represented by following Formulae (5a) and (5b):
• Ra—CH2—Rb (5a)Rc—CH2—Rd (5b)
• wherein Ra, Rb, Rc and Rd are the same or different and are each a hydrogen atom or a hydrocarbon group, and wherein Ra and Rb, Rc and Rd may be combined to form a ring together with the adjacent carbon atom, respectively;
• a pair of alcohol compounds represented by following Formulae (6a) and (6b):
• Ra—C(OH)—Rb (6a)Rc—C(OH)—Rd (6b)
• wherein Ra, Rb, Rc and Rd have the same meanings as defined above;
• and
• a pair of carbonyl compounds represented by following Formulae (7a) and (7b):
• Ra—C(═O)—Rb (7a)Rc—C(═O)—Rd (7b)
• wherein Ra, Rb, Rc and Rd have the same meanings as defined above, to react with oxygen, ammonia and water in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (A) in its ring:
• 36
• wherein X is one of an oxygen atom and an —OR group, and wherein R is one of a hydrogen atom and a hydroxyl-protecting group, to yield an azine compound represented by following Formula (3):
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• wherein Ra, Rb, Rc and Rd have the same meanings as defined above, or oxime compounds represented by following Formulae (4a) and/or (4b):
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• wherein Ra, Rb, Rc and Rd have the same meanings as defined above.