1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis

Benjamin Staskun; Theodorus Van Es

1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis

Benjamin Staskun^*, Theodorus Van Es

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-propenoate. With the use of ethyl 3-amino-2-butenoate as enamine the ultimate reaction product is a 2-methyl-4-arylamino-3-quinolinecarboxylate. The 2-CH₃ protons of the 4-iminoquinoline esters undergo exchange in D₂O/CDCl₃ at room temperature.

Original language	English
Pages (from-to)	92-99
Number of pages	8
Journal	South African Journal of Chemistry
Volume	51
Issue number	2
Publication status	Published - Jun 1998

Cite this

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title = "1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis",

abstract = "The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-propenoate. With the use of ethyl 3-amino-2-butenoate as enamine the ultimate reaction product is a 2-methyl-4-arylamino-3-quinolinecarboxylate. The 2-CH3 protons of the 4-iminoquinoline esters undergo exchange in D2O/CDCl3 at room temperature.",

author = "Benjamin Staskun and \{Van Es\}, Theodorus",

year = "1998",

month = jun,

language = "English",

volume = "51",

pages = "92--99",

journal = "South African Journal of Chemistry",

issn = "0379-4350",

publisher = "South African Chemical Institute",

number = "2",

}

TY - JOUR

T1 - 1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis

AU - Staskun, Benjamin

AU - Van Es, Theodorus

PY - 1998/6

Y1 - 1998/6

N2 - The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-propenoate. With the use of ethyl 3-amino-2-butenoate as enamine the ultimate reaction product is a 2-methyl-4-arylamino-3-quinolinecarboxylate. The 2-CH3 protons of the 4-iminoquinoline esters undergo exchange in D2O/CDCl3 at room temperature.

AB - The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-propenoate. With the use of ethyl 3-amino-2-butenoate as enamine the ultimate reaction product is a 2-methyl-4-arylamino-3-quinolinecarboxylate. The 2-CH3 protons of the 4-iminoquinoline esters undergo exchange in D2O/CDCl3 at room temperature.

UR - https://www.scopus.com/pages/publications/0032342679

M3 - Article

AN - SCOPUS:0032342679

SN - 0379-4350

VL - 51

SP - 92

EP - 99

JO - South African Journal of Chemistry

JF - South African Journal of Chemistry

IS - 2

ER -

1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis

Abstract

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