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

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

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 253 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.07.075

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✦ Synopsis

Unprecedented aromatization was observed during N-alkylation reactions of 1-methyl-3,4-dihydro-bcarboline-3-carboxylic acid methyl ester, giving rise to 9-alkyl-1-methyl-b-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-b-carboline-3-carboxylic acid methyl ester as the major product in good yield.

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