Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives

Keyur G. Brahmbhatt; Nafees Ahmed; Inder P. Singh; Kamlesh K. Bhutani

doi:10.1016/j.tetlet.2009.07.075

Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives

Keyur G. Brahmbhatt, Nafees Ahmed, Inder P. Singh, Kamlesh K. Bhutani

Research output: Contribution to journal › Article › Research › peer-review

9 Citations (Scopus)

Abstract

Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-β-carboline-3-carboxylic acid methyl esters. Inverse addition of base during a similar reaction resulted in a chemoselective alkylation to form novel 3-butyl-1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester as the major product in good yield.

Original language	English
Pages (from-to)	5501-5504
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.075
Publication status	Published - 30 Sept 2009
Externally published	Yes

Keywords

1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid
Aromatization
Chemoselective alkylation
N-Alkylation
Oxidation

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10.1016/j.tetlet.2009.07.075

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title = "Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives",

abstract = "Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-β-carboline-3-carboxylic acid methyl esters. Inverse addition of base during a similar reaction resulted in a chemoselective alkylation to form novel 3-butyl-1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester as the major product in good yield.",

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T1 - Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives

AU - Brahmbhatt, Keyur G.

AU - Ahmed, Nafees

AU - Singh, Inder P.

AU - Bhutani, Kamlesh K.

PY - 2009/9/30

Y1 - 2009/9/30

N2 - Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-β-carboline-3-carboxylic acid methyl esters. Inverse addition of base during a similar reaction resulted in a chemoselective alkylation to form novel 3-butyl-1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester as the major product in good yield.

AB - Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-β-carboline-3-carboxylic acid methyl esters. Inverse addition of base during a similar reaction resulted in a chemoselective alkylation to form novel 3-butyl-1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid methyl ester as the major product in good yield.

KW - 1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid

KW - Aromatization

KW - Chemoselective alkylation

KW - N-Alkylation

KW - Oxidation

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DO - 10.1016/j.tetlet.2009.07.075

M3 - Article

AN - SCOPUS:68349125265

SN - 0040-4039

VL - 50

SP - 5501

EP - 5504

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Aromatization and chemoselective alkylation of 1-methyl-3,4-dihydro-β-carboline-3-carboxylic acid and its derivatives

Abstract

Keywords

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