An effective new synthesis of 2-aminopyrrole-4-carboxylates

Demir, Ayhan Sıtkı
Emrullahoglu, M
Efficient syntheses of 2-aminopyrroles are presented starting from beta-dicarbonyl compounds, bromoacetonitrile, and amines. Alkylation of beta-dicarbonyl compounds with bromoacetonitrile furnished alpha-cyanomethyl-beta-dicarbonyl compounds. The condensation reaction of alpha-cyanomethyl-beta-dicarbonyl compounds with amines catalyzed by p-TsOH affords the corresponding enamines in good yields. Base catalyzed cyclization via the addition of an amine moiety to the carbon-nitrogen triple bond of nitrile furnished 2-aminopyrroles in high yields.


Clean and efficient microwave-solvent-free conversion of homochiral amines, alpha-amino alcohols and alpha-amino acids to their chiral 2-substituted pyrrole derivatives
Aydogan, F; Demir, Ayhan Sıtkı (Elsevier BV, 2005-03-21)
Efficient synthesis of 1,2-disubstituted homochiral pyrroles has been achieved by a two-component coupling of chloroenones and amine compounds on the surface of silica gel without any solvent under microwave irradiation.
New approaches to polysubstituted pyrroles and pyrrolinones from alpha-cyanomethyl-beta-ketoesters
Demir, Ayhan Sıtkı; Emrullahoglu, Mustafa; Ardahan, Gulben (Elsevier BV, 2007-01-08)
In this present paper, we report the efficient, regioselective one-pot synthesis of 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields via the zinc perchlorate-catalyzed addition of alcohols and thiols to the nitrile carbon of alpha-cyanornethyl-beta-ketoesters followed by annulation. The addition-annulation process is undertaken in aqueous solution to give 4,5-dihydro-5-oxo-1H-pyrrole-beta-carboxylates (pyrrolinones) in good yields. These 4,5-dihydro-5-oxo-1H-pyrrole-3-carboxylates are also ...
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
KIVRAK, Arif; Zora, Metin (Elsevier BV, 2014-01-28)
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and alpha,beta-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and alpha,beta-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and alpha,beta-alkynic aldehydes in a one-pot manner under basic conditions. The reactions ...
An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones
Turksoy, F; Wallis, JD; Tunca, U; Ozturk, T (Elsevier BV, 2003-10-06)
A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCHS)-1,3-dithiole-2-thiones (R-Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discu...
Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex
Erturk, Erkan; Demir, Ayhan Sıtkı (Elsevier BV, 2008-08-04)
The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph(3)P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed.
Citation Formats
A. S. Demir and M. Emrullahoglu, “An effective new synthesis of 2-aminopyrrole-4-carboxylates,” TETRAHEDRON, pp. 10482–10489, 2005, Accessed: 00, 2020. [Online]. Available: