The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines<sup>1</sup>

Taylor, Edward C.; Garcia, Edward E.

doi:10.1021/jo01031a002

Cited by 51 publications

(7 citation statements)

References 3 publications

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“…Compound 16 reacts with amines to form the new 5-(aminemethyl)-7-phenyl-isoxazolo [4,5-d]pyrimidine-3-carboxamide 17-20. It is well Scheme 1 known that isoxazole rings are readily cleaved by hydrogenation [18][19][20][21]. Thus the reduction of compound 16 followed by treatment with sodium borohydride in methanol at room temperature gave compound 21 with only one reduced double bond at position 6-7 from four.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Wagner

Al‐Kadasi

Becan

et al. 2010

Journal of Heterocyclic Chem

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A number of derivatives of isoxazolo [4,3-d]pyrimidine and isoxazolo [4,5-d]pyrimidine were prepared with potential anticancer activity. Condensation of 4-amino-5-benzoyl-isoxazolo-3-carboxylic acid hydrazide with ethyl orthoformate and then with different amines gave a series of 3-benzoyl-7-oxo-7H-isoxazolo[4,3-d]pyrimidin-6-yl-aryliden-formamidine. A series of 5-aminomethyl-7-phenyl-isoxazolo[4,5-d]pyrimidine-3-carboxamide was obtained from 4-amino-5-benzoylisoxazole-3-carboxamide with acetonitrile, and chloroacetonitrile with gaseous hydrogen chloride. Some of these compounds were tested for their cytotoxic activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Wagner

Al‐Kadasi

Becan

et al. 2010

Journal of Heterocyclic Chem

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“…The starting material, 5-amino-3-methylisoxazole-4-carboxylic acid 4 was prepared according to the method described by Taylor and Garcia [6] . Amino acid 4 was converted into mixed anhydride 5 as a result of the reaction with ethyl chloroformate in the presence of anhydrous pyridine.…”

Section: Resultsmentioning

confidence: 99%

“…All compounds were analyzed for C, H, N and analytical results were within ±0.4% of the theoretical values. Commercially available reagents and solvents were used without further purification.-The starting compounds 5-amino-3-methylisoxazole-4-carboxylic acid 4 was prepared according to the method described by Taylor and Garcia [6] .…”

Section: Quantitative Structure-activity Relationshipsmentioning

confidence: 99%

Immunomodulating Action and Structure-Activity Relationships of Substituted Phenylamides of 5-Amino-3-methylisoxazole-4-carboxylic Acid

Ryng¹,

Zimecki

Sonnenberg

et al. 1999

Arch. Pharm. Pharm. Med. Chem.

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A series of 5‐amino‐3‐methylisoxazole‐4‐carboxylic acid amides has been prepared by condensation of 5‐amino‐3‐methylisoxazole‐4‐carboxylic acid with ethyl chloroformate. The resulting mixed anhydride undergoes condensation with appropriate phenylamides to form the corresponding amides 6‐16. The compounds obtained were evaluated for their immunological activities in cultures of human peripheral blood mononuclear cells (PMBC). We found that the activities of the compounds in the proliferation test and in the lipopolysaccharide (LPS)‐induced cytokine production in PBMC cultures were differential. The stimulatory or inhibitory effects depended strongly on the origin and location of substituents in the phenyl ring which is described in the discussion and was supported by QSAR studies.

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“…Oxide (18).-The aminoisoxazole carbonitrile (17) (2.46 g) was added at 0 "C to a mixture of sulphuric acid (98%, 13 ml) and fuming nitric acid (95%; 1.36 g). The mixture was kept in a refrigerator at 9 "C for two days, then poured onto ice, and the pH adjusted to ca.…”

Section: 4-dihydro-5-methyl-4-oxoisoxazolo[54-d]-123-triazine 2-mentioning

confidence: 99%

1,2,3-Benzotriazine 2-oxides

Boulton¹,

Kiss²,

Saka³

1988

J. Chem. Soc., Perkin Trans. 1

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4-Methoxy-I ,2,3-benzotriazine, like the 4-methyl and 4-phenyl compounds, forms the 2-oxide on Noxidation; this is hydrolysed to the acidic 3,4-dihydr0-4-0~0-1,2,3-benzotriazine 2-oxide, which is Nmethylated by diazomethane at the 3-position. The 4-methoxy 2-oxide was converted into 4-amino-and 4-hydrazi no-der ivatives. 5 -Amino-3methyl isoxazole-2 -carbon itrile forms 3,4-d i hydro-5-methyl -4oxoisoxazolo[5,4-d] -1,2,3-triazine 2-oxide on reaction with nitric and sulphuric acids. The 15N n.m.r. spectra of some 1,2,3-benzotriazines and their N-oxides are reported.

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The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines¹

Cited by 51 publications

References 3 publications

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Immunomodulating Action and Structure-Activity Relationships of Substituted Phenylamides of 5-Amino-3-methylisoxazole-4-carboxylic Acid

1,2,3-Benzotriazine 2-oxides

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The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines1

Cited by 51 publications

References 3 publications

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Synthesis and pharmacological screening of derivatives of isoxazolo[4,3‐d]pyrimidine and isoxazolo[4,5‐d]pyrimidine

Immunomodulating Action and Structure-Activity Relationships of Substituted Phenylamides of 5-Amino-3-methylisoxazole-4-carboxylic Acid

1,2,3-Benzotriazine 2-oxides

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The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines¹