Zinc perchlorate catalyzed one-pot amination-annulation of alpha-cyanomethyl-beta-ketoesters in water. Regioselective synthesis of 2-aminopyrrole-4-carboxylates

Demir, Ayhan Sıtkı
Emrullahoglu, M
In this paper, we report the efficient and regioselective synthesis of 2-aminopyrrole-4-carboxylates as derivatives of conformationally restricted analogues of gamma-amino butyrates (GABA) via a zinc perchlorate catalyzed amination-annulation of alpha-cyanomethyl-beta-ketoesters under mild reaction conditions in water.


Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones
Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01)
The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
Enzyme catalyzed hydroxymethylation of aromatic aldehydes with formaldehyde. Synthesis of hydroxyacetophenones and (S)-benzoins
Demir, Ayhan Sıtkı; Ayhan, P; Igdir, AC; Duygu, AN (Elsevier BV, 2004-07-26)
Benzaldehyde lyase from the Pseudomonas Fluorescens catalyzed reaction of aromatic aldehydes with formaldehyde providing 2-hydroxy-1-arylethan-1-one in high yields via an acyloin linkage. Kinetic resolution of rac-benzoins with formaldehyde providing (S)-benzoins and 2-hydroxy-1-arylethan-1-one via C-C bond cleavage and a bond formation reaction.
Synthesis of thio- and furan-fused heterocycles: furopyranone, furopyrrolone, and thienopyrrolone derivatives
ERGUN, Merve; Dengiz, Çağatay; OZER, Merve Sinem; ŞAHİN, Ertan; BALCI, METİN (Elsevier BV, 2014-09-02)
We report herein the synthesis of a novel class of compounds, ethyl 4-oxo-4H-furo[3,2-c]pyran-6-yl carbonate, (7E)-7-[(dimethylamino)methylene]-4H-furo[3,2-c]pyran-4,6(7H)-dione, 5-oxo-N-phenyl-2,5-dihydro-4H-furo[3,2-b]pyrrole-4-carboxamide,and 5-oxo-N-phenyl-5,6-dihydro-4H-thieno[3,2-b] pyrrole-4-carboxamide starting from the corresponding acid derivatives. Intramolecular cyclization in the presence of thionyl chloride formed the target fused ring systems. Additional transformation was seen in the cycliza...
Manganese(III) acetate-mediated synthesis of biaryls under microwave irradiation
Demir, Ayhan Sıtkı; Findik, Hamide; SAYGILI, NEZİRE; Subasi, N. Tuna (Elsevier BV, 2010-02-06)
Manganese(Ill) acetate (Mn(OAc)(3))-mediated synthesis of biaryls and heterobiaryls starting from arylboronic acid was developed under microwave irradiation in high yields Microwaves were also used for the synthesis of Mn(OAc)(3) from KMnO4 and acetic acid Additional irradiation of this in situ generated Mn(OAc)3 with arylboronic acids, which in turn furnished the biaryls in high yields In a one pot reaction This IS superior from the point of view of yield, short reaction time, sensitive functional group to...
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.
Citation Formats
A. S. Demir and M. Emrullahoglu, “Zinc perchlorate catalyzed one-pot amination-annulation of alpha-cyanomethyl-beta-ketoesters in water. Regioselective synthesis of 2-aminopyrrole-4-carboxylates,” TETRAHEDRON, pp. 1452–1458, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57774.