The Reaction of Ethyl Ethoxymethylenecyanoacetate with Its Hydrazino Derivatives

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概要

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• The reaction of ethyl ethoxymethylenecyanoacetate with its hydrazino derivative in the presence of pyridine in ethanol at room temperature gave ethyl (4-ethoxycarbonyl-5-aminopyrazol-1-yl)methylenecyanoacetate(<B>6</B>) and two geometric isomers of ethyl (4-ethoxycarbonylpyrazol-5-ylamino)methylenecyanoacetate(<B>7</B>). Compound <B>6</B> itself, under the same conditions, rearranged to compound <B>7</B>. Both compounds, <B>6</B> and <B>7</B>, upon heating cyclized exclusively to the same product, diethyl 7-aminopyrazolo[1,5-<I>a</I>]pyrimidine-3,6-dicarboxylate(<B>8</B>). From the results of other combination reactions on methylenecyanoacetic ester homologs, a plausible reaction mechanism involving a rearrangement is discussed.

• 公益社団法人 日本化学会の論文

著者

• Midorikawa Hiroshi

  The Institute of Physical and Chemical Research

• Saito Koji

  Oyama Technical College

• Hori Isaburo

  The Institute of Physical and Chemical Research

• Igarashi Minoru

  The Institute of Physical and Chemical Research

関連論文

• Geometric Configurations of α-Cyano-β-methyl-β-alkylglycidic Esters
• The Syntheses of Heterocyclic Compounds by the Ternary Condensation of Malononitrile, Salicylaldehyde, and Aliphatic Ketones in the Presence of Ammonium Acetate
• The Reaction of Ethyl Ethoxymethylenecyanoacetate with Its Hydrazino Derivatives
• The Formation of Pyrazolo[1,5-a]pyrimidine Derivatives
• The Cyclization Products from Acetone with Cyanoacetic Esters
• Thiocyanoacetate. I. Reactions of Thiocyanoacetic Esters with Aldehydes
• Studies on Geometrical Isomerism by Nulear Magnetic Resonance. V. Stereochemistry of 5-Substituted 4-Alkoxycarbonyl-2-carbamoylimino-1,3-oxathiolanes
• The Paal-Knorr Condensation of Acetonylacetone with 5-Aminopyrazoles

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