.ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XV. The reaction of ethyl 3-nitro-2-alkenoate with bromine azide or bromine, and transformations of the products.

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概要

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• The reaction of ethyl (<I>Z</I>)-3-nitro-2-alkenoate (<B>1</B>) with one or two equivalents of bromine azide gave a one-to-one mixture of ethyl (<I>E</I>)-2-azido-3-nitro-2-alkenoate (<B>3</B>) and 4-ethoxycarbonyl-1,2,5-oxadiazole 2-oxide (<B>5</B>), or ethyl 3-bromo-2,2-diazido-3-nitroalkanoate (<B>6</B>), respectively, and the subsequent thermal and photochemical reactions of (<B>E</B>)-<B>3</B> gave 2-ethoxycarbonyl-3-nitro-l-azirine, together with a small amount of <B>5</B>. The addition of bromine to <B>1</B>, and the subsequent elimination of hydrogen bromide from the product, gave exclusively, the (<I>Z</I>)-2-bromo derivative (<B>9</B>). The reduction of <B>6</B> and <B>9</B> with diethyl phosphonate was examined, and the reaction mechanisms were discussed.

• 公益社団法人 日本化学会の論文

著者

• Suzuki Kaoru

  Laboratory of Animal Reproduction, School of Veterinary Medicine, Azabu University

• Shin Chung-gi

  Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University

• Yonezawa Yasuchika

  Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Suzuki Kaoru

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Shin Chung-gi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

関連論文

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• Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P
• Convenient Synthesis of the Central 3,6-Di(2-thiazolyl)-2-(4-thiazolyl)-pyridine Skeleton of a Macrocyclic Antibiotic, GE 2270 A
• Synthesis of a Fragment A Derivative of an Antibiotic, Nosiheptide
• Total Synthesis of Antibiotic, Micrococcin P, from 2, 3, 6-Polythiazolesubstituted Pyridine Skeleton[Fragment A-C]
• Synthesis of the Central Heterocyclic Skeleton of an Antibiotic, A10255
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• Syntheses of 2-[(1S,3S)-1-Amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid
• Dehydrooligopeptides. XVII. Practical Syntheses of All of the Diastereomers of N,N-Protected 2,3-Diaminobutanoic Acids from L-and D-Threonine Derivatives
• A Convenient Synthesis of Methyl 2-[2-(Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin
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• Practical Synthesis of Oligodehydroalanine Derivatives by Repetition of Stepwise Elongation of Serine Derivative and β-Elimination
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• Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures
• Total Synthesis of Bistratamides G and H from Various Kinds of ΔAla and ΔAbu-Containing Oligopeptides
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• Branched-Chain Sugars. I. On the Configuration of Branched-Chain Derivatives of 1,2 : 5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose
• Branched-chain Sugars. VIII. On the Configuration of Branched-chain Sugars from Methyl 3-O-Benzoyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose
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• .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XV. The reaction of ethyl 3-nitro-2-alkenoate with bromine azide or bromine, and transformations of the products.
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• α,β-Unsaturated Carboxylic Acid Derivatives. VIII. The Synthesis and Reaction of Esters N-Acyl-N-bromo-α-dehydroamino Acid
• Branched-Chain Sugars. II. On the Configuration of Branched-Chain Sugars from Methyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose
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