Nitrogen bridgehead compounds. Part 77. Addition reaction of 9‐methylene‐6,7,8,9‐tetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones

Gábor Tóth, Frank Janke, I. Hermecz, I. Bitter

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Abstract

Addition of bromine or thioacetic acid onto 6‐methyl‐9‐methylenetetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones is stereoselective and gives the cis 6‐Me,9‐CH substituted products. Addition is also stereoselective in respect to the C(9) and C(10) centers, and gives as the primary product the erythro diastereomer, which may then undergo epimerization to the threo isomer. Relative configuration and predominant conformation of the products were determined by 1D and 2D nmr methods.

Original languageEnglish
Pages (from-to)247-253
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume27
Issue number2
DOIs
Publication statusPublished - 1990

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Nitrogen Compounds
Bromine
Addition reactions
Isomers
Conformations
thioacetic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Nitrogen bridgehead compounds. Part 77. Addition reaction of 9‐methylene‐6,7,8,9‐tetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones",
abstract = "Addition of bromine or thioacetic acid onto 6‐methyl‐9‐methylenetetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones is stereoselective and gives the cis 6‐Me,9‐CH substituted products. Addition is also stereoselective in respect to the C(9) and C(10) centers, and gives as the primary product the erythro diastereomer, which may then undergo epimerization to the threo isomer. Relative configuration and predominant conformation of the products were determined by 1D and 2D nmr methods.",
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T1 - Nitrogen bridgehead compounds. Part 77. Addition reaction of 9‐methylene‐6,7,8,9‐tetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones

AU - Tóth, Gábor

AU - Janke, Frank

AU - Hermecz, I.

AU - Bitter, I.

PY - 1990

Y1 - 1990

N2 - Addition of bromine or thioacetic acid onto 6‐methyl‐9‐methylenetetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones is stereoselective and gives the cis 6‐Me,9‐CH substituted products. Addition is also stereoselective in respect to the C(9) and C(10) centers, and gives as the primary product the erythro diastereomer, which may then undergo epimerization to the threo isomer. Relative configuration and predominant conformation of the products were determined by 1D and 2D nmr methods.

AB - Addition of bromine or thioacetic acid onto 6‐methyl‐9‐methylenetetrahydro‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones is stereoselective and gives the cis 6‐Me,9‐CH substituted products. Addition is also stereoselective in respect to the C(9) and C(10) centers, and gives as the primary product the erythro diastereomer, which may then undergo epimerization to the threo isomer. Relative configuration and predominant conformation of the products were determined by 1D and 2D nmr methods.

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U2 - 10.1002/jhet.5570270225

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JF - Journal of Heterocyclic Chemistry

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