Reactions of uracils, 23. Subsequent reactions of 7-ethoxypyrimido[4,5-d]pyrimidines

Nucleophilic exchange, pyrimido[4,5:4′,5′]pyrimido[1,2-a]quinazolines, benzo[f]pyrimido[4,5:4′,5′]pyrimido[1,2-d][1,3,4]triazepine

Heinrich Wamhoff, Jürgen Muhr, Michael Horn, P. Sohár, A. Csámpai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The nucleophilic substitution of 7-ethoxypyrimido[4,5-d]pyrimidines 1a-d is described to afford with ammonia 7-amino derivative 2a, with glycine ester 3a, and with (±)2-phenylethylamine 4a, while reaction with amino acid ester hydrochlorides in DMSO at 150°C leads with remarkable ease to syn-elimination of ethylene to give tetraones 5a.b. DBN employed as base reacts with substitution and cleavage to pyrrolidinone-N-propylamino derivative 6. Pyridopyrimidines 1a-c and hydrazine hydrate afford the 7-hydrazino derivatives 7a-c which give with S,S-ketene acetal 8 the 7-(N-1′-pyrazolyl)-derivatives 9a-c. The 6-(2′-methoxycarbonylphenyl)-derivative 1d reacts with ammonia to the pyrimido-pyrimido carboxylate 6-ammonium betaine 10a and is converted into the tetracyclic pyrimido-pyrimido-quinazoline 10b by refluxing in DMSO. Short treatment of 1d with hydrazine gives 6-aminoquinazoline 11 as a pure product, while a prolonged heating leads to a nearly insoluble mixture of 11 and its isomer the 1,3,4-triazepine 12 as the main products and a third component in small amount, the structure of which could not be elucidated till now.

Original languageEnglish
Pages (from-to)365-376
Number of pages12
JournalHeterocyclic Communications
Volume5
Issue number4
Publication statusPublished - 1999

Fingerprint

Quinazolines
Pyrimidines
Uracil
hydrazine
Derivatives
Dimethyl Sulfoxide
Ammonia
Esters
Substitution reactions
Pyrrolidinones
Betaine
Acetals
Ammonium Compounds
Isomers
Glycine
Heating
Amino Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Reactions of uracils, 23. Subsequent reactions of 7-ethoxypyrimido[4,5-d]pyrimidines: Nucleophilic exchange, pyrimido[4,5:4′,5′]pyrimido[1,2-a]quinazolines, benzo[f]pyrimido[4,5:4′,5′]pyrimido[1,2-d][1,3,4]triazepine",
abstract = "The nucleophilic substitution of 7-ethoxypyrimido[4,5-d]pyrimidines 1a-d is described to afford with ammonia 7-amino derivative 2a, with glycine ester 3a, and with (±)2-phenylethylamine 4a, while reaction with amino acid ester hydrochlorides in DMSO at 150°C leads with remarkable ease to syn-elimination of ethylene to give tetraones 5a.b. DBN employed as base reacts with substitution and cleavage to pyrrolidinone-N-propylamino derivative 6. Pyridopyrimidines 1a-c and hydrazine hydrate afford the 7-hydrazino derivatives 7a-c which give with S,S-ketene acetal 8 the 7-(N-1′-pyrazolyl)-derivatives 9a-c. The 6-(2′-methoxycarbonylphenyl)-derivative 1d reacts with ammonia to the pyrimido-pyrimido carboxylate 6-ammonium betaine 10a and is converted into the tetracyclic pyrimido-pyrimido-quinazoline 10b by refluxing in DMSO. Short treatment of 1d with hydrazine gives 6-aminoquinazoline 11 as a pure product, while a prolonged heating leads to a nearly insoluble mixture of 11 and its isomer the 1,3,4-triazepine 12 as the main products and a third component in small amount, the structure of which could not be elucidated till now.",
author = "Heinrich Wamhoff and J{\"u}rgen Muhr and Michael Horn and P. Soh{\'a}r and A. Cs{\'a}mpai",
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T1 - Reactions of uracils, 23. Subsequent reactions of 7-ethoxypyrimido[4,5-d]pyrimidines

T2 - Nucleophilic exchange, pyrimido[4,5:4′,5′]pyrimido[1,2-a]quinazolines, benzo[f]pyrimido[4,5:4′,5′]pyrimido[1,2-d][1,3,4]triazepine

AU - Wamhoff, Heinrich

AU - Muhr, Jürgen

AU - Horn, Michael

AU - Sohár, P.

AU - Csámpai, A.

PY - 1999

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N2 - The nucleophilic substitution of 7-ethoxypyrimido[4,5-d]pyrimidines 1a-d is described to afford with ammonia 7-amino derivative 2a, with glycine ester 3a, and with (±)2-phenylethylamine 4a, while reaction with amino acid ester hydrochlorides in DMSO at 150°C leads with remarkable ease to syn-elimination of ethylene to give tetraones 5a.b. DBN employed as base reacts with substitution and cleavage to pyrrolidinone-N-propylamino derivative 6. Pyridopyrimidines 1a-c and hydrazine hydrate afford the 7-hydrazino derivatives 7a-c which give with S,S-ketene acetal 8 the 7-(N-1′-pyrazolyl)-derivatives 9a-c. The 6-(2′-methoxycarbonylphenyl)-derivative 1d reacts with ammonia to the pyrimido-pyrimido carboxylate 6-ammonium betaine 10a and is converted into the tetracyclic pyrimido-pyrimido-quinazoline 10b by refluxing in DMSO. Short treatment of 1d with hydrazine gives 6-aminoquinazoline 11 as a pure product, while a prolonged heating leads to a nearly insoluble mixture of 11 and its isomer the 1,3,4-triazepine 12 as the main products and a third component in small amount, the structure of which could not be elucidated till now.

AB - The nucleophilic substitution of 7-ethoxypyrimido[4,5-d]pyrimidines 1a-d is described to afford with ammonia 7-amino derivative 2a, with glycine ester 3a, and with (±)2-phenylethylamine 4a, while reaction with amino acid ester hydrochlorides in DMSO at 150°C leads with remarkable ease to syn-elimination of ethylene to give tetraones 5a.b. DBN employed as base reacts with substitution and cleavage to pyrrolidinone-N-propylamino derivative 6. Pyridopyrimidines 1a-c and hydrazine hydrate afford the 7-hydrazino derivatives 7a-c which give with S,S-ketene acetal 8 the 7-(N-1′-pyrazolyl)-derivatives 9a-c. The 6-(2′-methoxycarbonylphenyl)-derivative 1d reacts with ammonia to the pyrimido-pyrimido carboxylate 6-ammonium betaine 10a and is converted into the tetracyclic pyrimido-pyrimido-quinazoline 10b by refluxing in DMSO. Short treatment of 1d with hydrazine gives 6-aminoquinazoline 11 as a pure product, while a prolonged heating leads to a nearly insoluble mixture of 11 and its isomer the 1,3,4-triazepine 12 as the main products and a third component in small amount, the structure of which could not be elucidated till now.

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