Studies on the conformation of 1-aryl-1-nitrosoureas and related compounds.

Tanno, Masayuki; Sueyoshi, Shoko

doi:10.1248/cpb.35.1353

Cited by 3 publications

(7 citation statements)

References 6 publications

(6 reference statements)

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“…Spectral data: 1 H NMR δ 1.19 (t, J = 7.2 Hz, 3H), 4.08 (q, J = 7.2 Hz, 2H), 7.36 (dd, J = 7.2 Hz, 1.2 Hz, 1H), 7.48 (m, 2H), 7.53 (m, 2H); 13 C NMR δ 11.93, 39.42, 119.78, 127.54, 129.73, 141.64. 13 C NMR matches with literature report …”

Section: Methodssupporting

confidence: 89%

“…Spectral data: 1 H NMR δ 2.94 ( E , s, 3H), 3.68 ( Z , s, 3H), 4.80 ( Z , s, 3H), 5.30 ( E , s, 3H), 7.13 ( Z , m, 2H), 7.25–7.40 (m, 5H ( E ), 3H ( Z )); 13 C NMR δ 30.2 ( E ), 38.7 ( Z ), 48.0 ( Z ), 128.2 ( Z ), 128.3 ( E ), 128.6 ( Z ), 128.8 ( E ), 129.1 ( Z ), 129.3 ( E ), 134.0 ( Z ), 134.7 ( E ). 13 C NMR matches with literature report …”

Section: Methodssupporting

confidence: 89%

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Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

2011

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Aliphatic or aromatic N,N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o-iodosylbenzoic acid (IBA)/R(4)NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R(4)NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F(-) > Cl(-) > Br(-) ∼ I(-). Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.

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Section: Methodssupporting

confidence: 89%

Section: Methodssupporting

confidence: 89%

Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

2011

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“…The conformation of the nitrosoureas (4 7) was identified by comparing the chemical shifts with those of 1-methyl-3,3-(pentanediy1)-1-nitrosourea (only E form) and 1-isopropy1-3,3-(pentanediy1)-1-nitrosourea (a mixture of E and Z forms).12) The NO group is in the E relationship to the CO group in both the 1-nitrosoureas and the 3-nitroso isomers, in other TABLE II. 13C-Chemical Shifts") (ppm) of Nitrosoureas (4-7), Ureas (9, 10), Nitro Compounds (11,12) and Carbamates (21) words, the NO group of the 1-nitrosoureas is directed toward the aryl ring and that of the 3-nitroso isomers is directed toward the N3-alkyl group.…”

Section: Nitrosation;mentioning

confidence: 99%

“…The disubstituted 1-nitrosoureas (4,5) and the N-nitrosoacetanilides (8) afforded the corresponding 2-nitroaryl compounds (11,12) similarly to the trisubstituted nitrosoureas (1). The nitration yields are shown in Table III.…”

Section: Nitration and Isomerizationmentioning

confidence: 99%

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Preparation and properties of 3-alkyl-1-arylnitrosoureas and related compounds.

Tanno

Sueyoshi

1987

CHEMICAL & PHARMACEUTICAL BULLETIN

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Nitrosation of 3-alkyl-1-arylureas was investigated with sodium nitrite in 99% formic acid or with isoamyl nitrite in chloroform. The preparation of 3-alkyl-1-aryl-1-nitrosoureas was effectively performed by using isoamyl nitrite in the absence of acids, since the 1-nitrosoureas were isomerized to the 3-nitroso isomers by acids. The carbon-13 nuclear magnetic resonance and infrared spectral properties of the products were examined and their structural features are discussed.It was found that 3-alkyl-1-aryl-1-nitrosoureas decomposed to form alkyl isocyanates and 3-alky1-1-(2-nitroaryOureas in carbon tetrachloride. 1,3-Rearrangement and transnitrosation also took place in this solvent.We recently reported1) on the chemical properties of novel trisubstituted N-nitrosoureas. 3,3-Diethyl-1-(4-tolyl)-1-nitrosourea (1b) decomposed to give the triazene (2b) and the nitro compound (3) in chloroform or carbon tetrachloride at room temperature, while the 2-tolyl derivative (la) gave mainly the triazene (2a) under similar conditions. The reaction of nitrosoureas to give the triazenes is of interest because several derivatives of 3-alkyl-1 -phenyltriazenes and 3,3-dialkyl-1-phenyltriazenes have been reported to show antitumor activity.2) Therefore, we examined whether 3-alkyl-1-aryltriazenes were produced or not by the decomposition of 3-alkyl-1-arylnitrosoureas (4, 5).A number of reports have dealt with the antitumor activities and the chemical properties of 1,3-dialkylnitrosoureas.3-5) In a study of the nitrosation of 3-alkyl-1-phenylureas, Johnston et al.5) obtained a mixture of 1-nitrosoureas and the 3-nitroso isomers. Kamiya and co-workers6-8) described the synthesis and decomposition of 1,3-diaryl-1-nitrosoureas and related compounds. However, there are few data on the chemical properties of 3-alkyl-1-ary1-1-nitrosoureas, especially 3-methyl-l-phenyl-1-nitrosourea (4c), because of the difficulty of its isolation. In the nitrosation of 3-methyl-1 -phenylurea (9c), the 3-nitrosourea (6c) is produced overwhelmingly and the desired 1-nitrosourea (4c) can not be obtained by the ordinary method using sodium nitrite and acids. In this paper, we wish to present the preparation and properties of 3-alkyl-1-aryl-1-nitrosoureas and related compounds. Preparation of NitrosoureasN-Nitrosoureas (4 7) and N-nitrosoacetanilides (8) were prepared by nitrosation of the corresponding ureas (9, 10) and acetanilides, respectively. The ureas (9, 10) as starting materials were prepared by the reaction of aryl isocyanates with alkylamines or anilines with alkyl isocyanates in ether. Since the nitroso compounds were unstable at room temperature, they were quickly purified by silica gel column chromatography with a mixture of n-hexane and ether under cooling.1)The nitrosation of 1-aryl-1-isopropylureas (10) with sodium nitrite and 99% formic acid

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Nucleoside analogues. Part 12. The anomalous¹⁹F NMR spectrum of B.3996, a molecular combination of 5-fluorouracil and N-(2-chloroethyl)-N-nitrosourea and synthesis of its N′-nitroso isomer and related compounds

McCormick¹,

Mcelhinney²,

McMurry³

et al. 1991

J. Chem. Soc., Perkin Trans. 1

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Studies on the conformation of 1-aryl-1-nitrosoureas and related compounds.

Cited by 3 publications

References 6 publications

Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

Preparation and properties of 3-alkyl-1-arylnitrosoureas and related compounds.

Nucleoside analogues. Part 12. The anomalous¹⁹F NMR spectrum of B.3996, a molecular combination of 5-fluorouracil and N-(2-chloroethyl)-N-nitrosourea and synthesis of its N′-nitroso isomer and related compounds

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Studies on the conformation of 1-aryl-1-nitrosoureas and related compounds.

Cited by 3 publications

References 6 publications

Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

Nitromethane with IBX/TBAF as a Nitrosating Agent: Synthesis of Nitrosamines from Secondary or Tertiary Amines under Mild Conditions

Preparation and properties of 3-alkyl-1-arylnitrosoureas and related compounds.

Nucleoside analogues. Part 12. The anomalous19F NMR spectrum of B.3996, a molecular combination of 5-fluorouracil and N-(2-chloroethyl)-N-nitrosourea and synthesis of its N′-nitroso isomer and related compounds

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Nucleoside analogues. Part 12. The anomalous¹⁹F NMR spectrum of B.3996, a molecular combination of 5-fluorouracil and N-(2-chloroethyl)-N-nitrosourea and synthesis of its N′-nitroso isomer and related compounds