Rearrangement of 1-Substituted 3-(3-Pyridylmethyl) nitrosoureas to Their N-Nitroso Isomers in the Presence of Acids
スポンサーリンク
概要
- 論文の詳細を見る
1-(2-Chloroethyl)-(IIa), 1-isopropyl-(IIb), 1-isobutyl- (IIc) and 1-cyclohexyl-1-nitroso-3-(3-pyridylmethyl) urea (IId) isomerized to the corresponding 3-nitroso isomers (IIIa-d) in formic acid. This type of rearrangement was also observed in acetic acid, 10% hydrochloric acid, 10% sulfuric acid, methanol saturated with hydrogen chloride, and thionyl chloride. However, 1-isopropyl- (IIIb) and 1-cyclohexyl-3-nitroso-3-(3-pyridylmethyl) urea (IIId), in which the N^1 substituents are bulky, hardly isomerized to the 1-nitrosoureas (IIb, d). Transnitrosation of 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea (IIa) with 1-methyl-3-(2-pyridylmethyl) urea gave the denitrosated compound (Ia) and a newly nitrosated compound, 1-methyl-1-nitroso-3-(2-pyridylmethyl) urea (V). It is suggested that this type of rearrangement is an acid-catalyzed, intermolecular rearrangement governed by the steric effect of the N^1 substituents.
- 公益社団法人日本薬学会の論文
- 1981-05-23
著者
-
神谷 庄造
National Institute of Hygienic Sciences, University of Tokyo
-
末吉 祥子
National Institute of Hygienic Sciences
-
神谷 庄造
National Institute Of Hygienic Sciences
関連論文
- Degradation of 1,3-Diaryl-1-nitrosoureas in Aqueous Solutions and in Organic Solvents(Organic,Chemical)
- Cyclization of 1-Aryl-1-nitroso-3-(2-pyridymethyl)ureas to 2-Aryl-5-(2-pyridyl)-2,4-dihydro-1,2,4-triazol-3-ones
- Synthesis, Chemical Properties and Mutagenicity of 1,6- and 3,6-Dinitrobenzo[a]pyrenes
- Synthesis of Antitumor Pyridine and Pyridazine N-Oxides having (2-Chloroethyl) nitrosoureidomethyl and Bis (2-chloroethyl)-aminomethyl Groups
- Antitumor Activity of 4-Nitropyridazine 1-Oxides and Related Compounds for AH-13
- Mutagenic and Prophage-inducing Activities of 1-Alkyl-3-nitrol-nitrosoguanidines
- Studies on Pyridazine 1,2-Dioxides. I. Syntheses of Pyridazine 1,2-Dioxides
- Reactions of 1-Nitroso-1-phenyl-3-(4-pyridylmethyl)ureas
- Cyclization of (2-Hydroxyethyl) urea Derivatives to Give 3-Nitroso-2-oxazolidinones under Usual Nitrosation Conditions
- Action Mechanism of Anti-AH13 Activity of 1,3-Diaryl-1-nitrosoureas and Related Compounds
- Nitrosation of 1,3-Diarylureas with Nitrosyl Chloride, Dinitrogen Trioxide and Dinitrogen Tetroxide in Dimethylformamide
- Antitumor Activity of 2-Acylamino-1,3,4-thiadiazoles and Related Compounds
- Thermal Decomposition of 1,3-Diaryl-1-nitrosoureas in Benzene
- Antitumor Activity of 3-Nitroso-2-oxazolidones
- N-アルキル-N-ニトロソウレタン類の製造(資料)
- Thermolysis of N-Aryl-N-nitrosoureas to Afford Aryl Isocyanates and Nitrosamines via O-Nitrosoisourea Intermediates
- 1,3-Nitroso Rearrangement and Transnitrosation of 1-Aryl-3-benzyl-1-nitrosoureas Which Decompose to Liberate Nitrosyl Radical under Mild Conditions
- Different Sensitivities of Rat Ascites Hepatoma AH13 and Mouse Lymphoid Leukemia L1210 Cells to Typical N-Nitrosoureas
- Reactions of 1-(2-Chloroethyl)-1-nitroso-3-(3-pyridylmethyl) urea N_-Oxide with Several Biological Model Compounds
- Nitrosation of 1-Substituted 3-(2-Pyridylmethyl) ureas and Related Compounds
- Syntheses of Arylcyanotriazenes and Related Compounds
- Rearrangement of 1-Substituted 3-(3-Pyridylmethyl) nitrosoureas to Their N-Nitroso Isomers in the Presence of Acids
- Synthesis of 4-Azidoquinoline 1-Oxides and Related Compounds
- Syntheses of 4-(3-Cyano-1-triazeno) pyridazine 1-Oxides Related Compounds
- Syntheses of 4-(3-Cyano-1-triazeno) pyridines and Related Compounds
- Tumors of the upper digestive tract of ACI/N rats given N-propyl-N-nitrosourethan in the drinking water
- Studies on Pyridazine 1,2-Dioxides. IV. Reduction and Substitution of 4-Nitro-3,6-dimethylpyridazine 1,2-Dioxide
- Syntheses of 3- and 4-Alkylaminomethylpyridazines
- The Alkylaminomethylation of Pyridazinol N-Oxides. V. The Reaction of 3-Pyridazinol 1-Oxide with Formalin and Hydrohalogenic Acids
- The C-Alkylaminomethylation of Pyridazinol N-Oxides. III. The Mannich Reaction of 5-Pyridazinol 1-Oxide
- The C-Alkylaminomethylation of 3-Pyridazinol 1-Oxide Derivatives. II. The C-Alkylaminomethylation of 6-Substituted 3-Pyridazinol 1-Oxides.
- Transnitrosation by N-Aryl-N-nitrosoureas : NO-Carrying O-Nitrosoisourea
- Preparation and Properties of 3-Alkyl-1-arylnitrosoureas and Related Compounds(Organic,Chemical)
- Studies on the Conformation of 1-Aryl-1-nitrosoureas and Related Compounds(Organic,Chemical)
- Preparation and Properties of Novel Trisubstituted N-Nitrosoureas which Decompose to Afford Triazenes and Nitro Compounds under Mild Conditions
- Reaction of N-Haloamide. VII. A Cleavage Reaction of Ether with N, N-Dihalobenzenesulfonamide. (2). Reactions of Tetrahydrofuran with N, N-Dibromobenzenesulfonamide, N-Bromosuccinimide, or Bromine. (1)
- Potential Anti-cancer Agents. XII. Synthesis of 4-Azido-3,6-dimethoxypyridazine Derivatives.
- Potential Anti-cancer Agents. XI. Synthesis of 4- and 5-Azidopyridazine 1-Oxide.
- Potential Anti-cancer Agents. X. Syntheses and Reactions of 3- and 6-Azidopyridazine 1-Oxide.
- Potential Anti-cancer Agents. II. 4-Azidoquinoline and 4-Azidopyridine Derivatives.
- The C-Alkylaminomethylation of Pyridazinol N-Oxides. IV. The Mannich Reaction of 3-and 5-Pyridazinol 1-Oxides using Primary Amines
- Nitrosation of 1-(2-Chloroethyl)-and 1-Cyclohexyl-3-(3-pyridyl) methylureas
- Pyridine Analogs of 1-Methyl-3-nitro-1-nitrosoguanidine and Related Compounds
- Syntheses of 1-Alkoxy-3,6-dimethyl-5-nitro-4 (1H)-pyridazinones and Related Compounds
- The Mannich Reaction of 3,6-Dimethyl-5-hydroxypyridazine 1-Oxide
- Studies on Fused Hydrazines. IV. Some Rearrangement Reactions of 4-Methyl-2,3,5,10-tetrahydro-1H-pyrazolo [1,2-b] phthalazinium Iodide and Related Compounds to N-Aminoalkylisoindole or N-Aminoalkyl-pyrrole
- A Convenient Synthesis of 1-(2-Halogenoethyl)-3-nitro-1-nitrosoguanidines
- Studies on Fused Hydrazines. III. The Alkaline Decomposition of 2,3,5,10-Tetrahydro-1H-pyrazolo [1,2-b] phthalazine Methiodide and Related Compounds
- Studies on Fused Hydrazines. II. The Stevens-Type Rearrangement of 2,3,5,10-Tetrahydro-1H-pyrazolo [1,2-b] phthalazin-5-one Methiodide and Related Compounds
- 窒素複素環化合物のPrototropic Tautomerismに関する研究(第3報) : Phthalic Hydrazide環のLactam-NHを含むRing-Chain Tautomerismにおける立体特異性について
- Synthesis of 2,3,5,10-Tetrahydro-1H-pyrazolo[1,2-b]phthalazines
- Studies on Prototropic Tautomerism in Nitrogen Heterocyclic Compounds. II. A Ring-Chain Tautomerism in 3-Hydroxy-6-(2-oxocycloalkyl)-methyl-2(1H)-pyridone and 3-Hydroxy-6-(3-oxoalkyl)-2(1H)-pyridone Derivatives
- Studies on Prototropic Tautomerism in Nitrogen Heterocyclic Compounds. I. The Mannich Reaction of 2(1H)-Pyridone and 3-Hydroxy-2(1H)-pyridone
- Ring-Substituted α-Amino Acids. I. The Michael-type Addition of Maleic Hydrazide and Related Compounds leading to the α-Amino Acids.
- Ring-substituted α-Amino Acids. II. The Reaction of Cyclic Lactams with Methyl Vinyl Ketone leading to the α, γ-Diaminobutyric Acid Derivatives.