Synthesis of 3-(alkylamino)-, 3-(alkoxy)-, 3-(aryloxy)-, 3-(alkylthio)-, and 3-(arylthio)-1,2,4-triazines by using a unified route with 3-(methylsulfonyl)-1,2,4-triazine

Da Hua Shi, Jitendra R. Harjani, Robert W. Gable, Jonathan B. Baell

Research output: Contribution to journalArticleResearchpeer-review

Abstract

In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.

Original languageEnglish
Pages (from-to)2842-2850
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number16
DOIs
Publication statusPublished - 1 Jun 2016

Keywords

  • Aromatic substitution
  • Nitrogen heterocycles
  • Nucleophiles
  • Oxidation
  • Synthetic methods

Cite this

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title = "Synthesis of 3-(alkylamino)-, 3-(alkoxy)-, 3-(aryloxy)-, 3-(alkylthio)-, and 3-(arylthio)-1,2,4-triazines by using a unified route with 3-(methylsulfonyl)-1,2,4-triazine",
abstract = "In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.",
keywords = "Aromatic substitution, Nitrogen heterocycles, Nucleophiles, Oxidation, Synthetic methods",
author = "Shi, {Da Hua} and Harjani, {Jitendra R.} and Gable, {Robert W.} and Baell, {Jonathan B.}",
year = "2016",
month = "6",
day = "1",
doi = "10.1002/ejoc.201600267",
language = "English",
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pages = "2842--2850",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
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}

Synthesis of 3-(alkylamino)-, 3-(alkoxy)-, 3-(aryloxy)-, 3-(alkylthio)-, and 3-(arylthio)-1,2,4-triazines by using a unified route with 3-(methylsulfonyl)-1,2,4-triazine. / Shi, Da Hua; Harjani, Jitendra R.; Gable, Robert W.; Baell, Jonathan B.

In: European Journal of Organic Chemistry, Vol. 2016, No. 16, 01.06.2016, p. 2842-2850.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Synthesis of 3-(alkylamino)-, 3-(alkoxy)-, 3-(aryloxy)-, 3-(alkylthio)-, and 3-(arylthio)-1,2,4-triazines by using a unified route with 3-(methylsulfonyl)-1,2,4-triazine

AU - Shi, Da Hua

AU - Harjani, Jitendra R.

AU - Gable, Robert W.

AU - Baell, Jonathan B.

PY - 2016/6/1

Y1 - 2016/6/1

N2 - In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.

AB - In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.

KW - Aromatic substitution

KW - Nitrogen heterocycles

KW - Nucleophiles

KW - Oxidation

KW - Synthetic methods

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