172. o-Amino-ketones of the acetophenone and benzophenone types

Simpson, Jean; Atkinson, C. M.; Schofield, K.; Stephenson, O.

doi:10.1039/jr9450000646

Cited by 42 publications

(34 citation statements)

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“…~ieatment of the diazonium salt of 5 with an aqueous solution of the primary alkylamine affords the 4-hydroxy-3-alkyl-l,2,3-benzotriazine (7). The spectroscopic properties of the ~roducts of these reactions are consistent with the cvclic benzotriazine structure (7) rather than the open-chain triazene valence tautomer (6).…”

Section: Discussionsupporting

confidence: 58%

“…The cyclic products are stable crystalline solids which show spectroscopic features consistent with the assigned triazine structure (9). The ir spectra show similar characteristics to the C-4 unsubstituted analogues (7). Carbonyl absorption is absent in the spectra of compounds 912-e and hydroxyi absorption is evident, but much broader (2560-3400 cm-') than in the spectra of compounds 7a-d.…”

Section: Discussionmentioning

confidence: 51%

“…4-Hydroxy-3-alkyl (ary1)-1,2,3(4H)-benzotriazines (7) General procedure o-Aminobenzaldehyde (5) was prepared immediately before use by reduction of o-nitrobenzaldehyde with ammonia and ferrous sulphate according to the method of Smith and Opie (5). o-Aminobenzaldehyde (1.44 g, 0.012 mol) was ground in a mortar with solid sodium nitrite (0.83 g, 0.012 mol) to a fine homogeneous powder.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 4-hydroxy-3,4-dihydro-1,2,3-benzotriazines via 2-(3-alkyl-1-triazeno)benzaldehydes and 2-(3-alkyl-1-triazeno)benzophenones

Faye¹,

Vaughan²,

Hooper³

1983

Can. J. Chem.

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Diazotization of o-aminobenzaldehyde, followed by immediate coupling of the diazonium salt with primary alkylamines, affords unstable l-aryl-3-alkyltriazenes which immediately cyclize to the 4-hydroxy-3-alkyl-1,2,3-benzotriazines. Analogous reaction of o-aminobenzophenones affords stable 4-aryl-4-hydroxy-3-alkyl-1,2,3-benzotriazines. The 4-hydroxytriazine derived from o-anthraniloylbenzoic acid undergoes further cyclization spontaneously to a novel spiro-1,2,3-triazine-furan. Diazotization of o-aminopropiophenone and coupling to methylamine affords a surprisingly stable 4-alkyl-4-hydroxytriazine. Preliminary assay of the biological activity of the 4-hydroxytriazines shows significant cytotoxicity of two members of the series towards M21 melanoma cells in vitro.

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Section: Discussionsupporting

confidence: 58%

Section: Discussionmentioning

confidence: 51%

Section: Methodsmentioning

confidence: 99%

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Synthesis of 4-hydroxy-3,4-dihydro-1,2,3-benzotriazines via 2-(3-alkyl-1-triazeno)benzaldehydes and 2-(3-alkyl-1-triazeno)benzophenones

Faye¹,

Vaughan²,

Hooper³

1983

Can. J. Chem.

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“…[10] The tolerence of ketone functionalities to iron-catalyzed nitro reduction is well precedented in the literature [1a,11] and with yields of 77% and 85% for p-aminoacetophenone and m-aminoacetophenone under ultrasonic irradiation respectively, our conditions also allow complete selectivity for the nitro substituent over the ketone moiety. Both of these compounds have been reported in the literature with yields of 92% [1a] and 80% [12] for the para-and meta-substituted compounds respectively, and although the former yield is higher than our reported yield, the reaction was done under high pressure at a temperature of 210 °C for 2 h with water as solvent.…”

mentioning

confidence: 54%

Aryl Nitro Reduction with Iron Powder or Stannous Chloride under Ultrasonic Irradiation

Gamble

Garner

Gordon

et al. 2007

Synthetic Communications

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The selective reduction of aryl nitro compounds in the presence of sensitive functionalities, including halide, carbonyl, nitrile and ester substituents under ultrasonic irradiation at 35 kHz is reported in yields of 39-98%. Iron powder proved superior to stannous chloride with high tolerance of sensitive functional groups and high yields of the desired aryl amines in relatively short reaction times. Simple experimental procedure and purification also make the iron reduction of aryl nitro compounds advantageous over other methods of reduction.

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“…This compound was prepared in four steps by bromination of 3-nitrobenzoic acid (12), [25] reduction of the carboxylic acid, [26] protection of the resulting alcohol as a MOM ether, [27] and a Bechamp reduction of the nitro group (Scheme 6). [28] The overall yield was 61 % over four steps. Building block 18 was converted into boronic ester 20 by a Miyaura reaction (Scheme 7).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Isomerization Studies of Cyclotrisazobiphenyl

Reuter

Wegner

2011

Chemistry A European J

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We report an efficient synthesis of cyclotris[(E)-3'-(biphenyl-3-yldiazenyl)] compounds (CTBs). An unsubstituted CTB molecule is accessible in four steps in 10% yield overall, whereas a hexa(methoxymethyl ether) CTB analogue was prepared in nine steps (26% yield). The final macrocyclization step was accomplished in up to 80% yield by using a metal-template effect. Furthermore, the photochromic properties were investigated, and all four isomers were detected and characterized by NMR spectroscopy. A strong influence from the solvent and the irradiation wavelength on the switching process was observed. Irradiation in pyridine yielded the highest amount of the all-Z isomer in the photostationary state. For a full conversion to the all-E isomer, the reaction has to be heated to 45 °C. The isomerization to the all-E isomer is slow at room temperature, with a half-life time of the all-Z isomer of more than nine days in dimethyl sulfoxide (DMSO). Conditions were established to access each possible isomer as the major component in the photostationary state.

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172. o-Amino-ketones of the acetophenone and benzophenone types

Cited by 42 publications

References 0 publications

Synthesis of 4-hydroxy-3,4-dihydro-1,2,3-benzotriazines via 2-(3-alkyl-1-triazeno)benzaldehydes and 2-(3-alkyl-1-triazeno)benzophenones

Synthesis of 4-hydroxy-3,4-dihydro-1,2,3-benzotriazines via 2-(3-alkyl-1-triazeno)benzaldehydes and 2-(3-alkyl-1-triazeno)benzophenones

Aryl Nitro Reduction with Iron Powder or Stannous Chloride under Ultrasonic Irradiation

Synthesis and Isomerization Studies of Cyclotrisazobiphenyl

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