1,3-Oxazines and Related Compounds. IX. Alkylation, Acylation, and Cleavage Reaction of 6-Methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine

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概要

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• Alkylation of the title compound (2) with alkyl halides in the presence of Et_3N proceeded exclusively on the sulfur atom to give the S-alkyl-1,3-oxazine derivatives. Acylation with acylchlorides took place regioselectively on the nitrogen atom, giving the N-acyl derivatives. 1,3-Oxazine 2 was found to undergo cleavage of the ring into acetylketene and thiocyanic acid. Hence, treatment of 2 with alkyl halides in the presence of K_2CO_3gave alkyl thiocyanates ; treatment with active methylene compounds afforded γ-pyrone derivatives. N-Acyl derivatives of 2 also underwent thermal cleavage of the ring, leading to the corresponding acyl isothiocyanates.

• 社団法人日本薬学会の論文
• 1984-08-25

著者

• 森田 恭夫

  Tohoku College of Pharmacy

関連論文

• 1,3-Oxazines and Related Compounds. XII. : Facile Synthesis of 2,4-Disubstituted 6H-1,3-Oxazin-6-ones
• 1,3-Oxazines and Related Compounds. X. Ring Transformation of 1,3-Oxazin-4-ones into Pyridine Derivatives
• 1,3-Oxazines and Related Compounds. IX. Alkylation, Acylation, and Cleavage Reaction of 6-Methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
• 1,3-Oxazines and Related Compounds. VIII. Reaction of 6-Methyl-2-phenyl-4H-1,3-oxazin-4-one with Lactams and Their Derivatives

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