New reactions of deoxyvasicinone. Part 6

…, KI Kinnear, R Norrie, N Ringan…

Index: Dunn, A. D.; Kinnear, K. I.; Norrie, R.; Ringan, N.; Martin, D. Journal of Heterocyclic Chemistry, 1987 , vol. 24, p. 175 - 180

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Citation Number: 2

Abstract

Abstract Several acylated derivatives of deoxyvasicinone 1 and its analogues were shown to exist as enols. The 3-hydroxymethyl derivative of 1 was shown to undergo rapid dehydration and products derived from an intermediate 3-methylene compound were obtained. Novel oxazepino analogues of 1 are reported.

 Related Synthetic Route
2-Aminoethanol Structure

141-43-5

2-Aminoethanol

N-Acetylanthranilic acid Structure

89-52-1

N-Acetylanthran...

~36%

3-(2-hydroxyethyl)-2-methylquinazolin-4-one Structure

10376-59-7

3-(2-hydroxyeth...

Formaldehyde Structure

50-00-0

Formaldehyde

2,3-Dihydropyrrolo[2,1-b]quinazolin-9(1H)-one Structure

530-53-0

2,3-Dihydropyrr...

~15%

2,3-dihydro-3,3-dihydroxymethylpyrrolo[2,1-b]quinazolin-9(1H)-one Structure

111970-07-1

2,3-dihydro-3,3...

2,3-dihydro-3-ethoxymethyl-3-hydroxymethylpyrrolo[2,1-b]quinazolin-9(1H)-one Structure

111970-08-2

2,3-dihydro-3-e...

Detail
Isatoic anhydride Structure

118-48-9

Isatoic anhydride

3-Chloropropanoyl chloride Structure

625-36-5

3-Chloropropano...

~%

W-2429 Structure

37795-69-0

W-2429

N-Acetylanthranilic acid Structure

89-52-1

N-Acetylanthran...

~%

3-(2-hydroxyethyl)-2-(2-phenylethenyl)quinazolin-4-one Structure

68501-37-1

3-(2-hydroxyeth...

3-(2-hydroxyethyl)-2-methylquinazolin-4-one Structure

10376-59-7

3-(2-hydroxyeth...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~39%

3-(2-benzoyloxyethyl)-2-(2-phenylethenyl)quinazolin-4(3H)-one Structure

111970-09-3

3-(2-benzoyloxy...

3-(2-hydroxyethyl)-2-(2-phenylethenyl)quinazolin-4-one Structure

68501-37-1

3-(2-hydroxyeth...

N/A Structure

22462-27-7

N/A

~31%

3,4-dihydro-2H-oxazino[3,2-b]quinazolin-10-one Structure

51866-11-6

3,4-dihydro-2H-...

Methyl 2-aminobenzoate Structure

134-20-3

Methyl 2-aminob...

~%

3,4-dihydro-2H-oxazino[3,2-b]quinazolin-10-one Structure

51866-11-6

3,4-dihydro-2H-...

2,3-dihydro-3-hydroxymethylenepyrrolo(2,1-b)quinazolin-9(1H)-one Structure

92883-81-3

2,3-dihydro-3-h...

~27%

2,3,4a,4-tetrahydro-3-methylpyrrolo[2,1-b]quinazolin-9-(1H)-one Structure

111970-06-0

2,3,4a,4-tetrah...

3-methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one Structure

94169-31-0

3-methyl-2,3-di...


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