Showing papers by "Branko Stanovnik published in 2001"
TL;DR: In this paper, aplysinopsin analogues were prepared by a simple coupling of N, N -(dimethylamino)methylidene substituted hydantoin, thiohydantoin and thiazolone derivatives, with indole derivatives.
40 citations
TL;DR: The first example of a Wolff rearrangement in the fused cyclic α-diazoamide series was reported in this paper, where the 4-oxoquinolizine-3-diazonium tetrafluoroborates 7a and 7b were transformed into the 3-carboxylates 9a−h.
14 citations
TL;DR: In this article, a simple stereoselective synthesis of 2Z and 2Z, 1′E alkyl 3-acyloxy-2-(2,2-disubstituted ethenyl) aminopropenoates 4 from alkyyl 2-(2.2, 2, 2-dimethylaminopro-enoates) amino-3-dimethyl) was presented in 12-91% yield.
8 citations
TL;DR: In this paper, a 2,3-dihydro-1, 3-dioxo-1H-isoindol-2-yl)acetate and bis(dimethylamino)-tert-butoxymethane were treated with various amines and hydrazines to afford corresponding amino substituted products.
Abstract: Ethyl (Z)-2-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)-3-(dimethylamino)propenoate was prepared in one step from ethyl (2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)acetate and bis(dimethylamino)-tert-butoxymethane and treated with various amines and hydrazines to afford the corresponding amino substituted products. Reactions of the titled compound with N,N'-, C,N-, and C,O'-ambident nucleophiles in refluxing acetic acid furnished the corresponding fused pyrimidinones, quinolizinones, and pyranones.
6 citations
TL;DR: Alkyl 2]-2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates 3 and 4 were transformed with C-and N-nucleophiles into β-heteroaryl-α,β-didehydro-α-amino acid derivatives.
6 citations
TL;DR: In this article, a simple two-step synthesis, starting from heterocyclic α-amino compounds and methyl (Z)-2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate followed by catalytic hydrogenation, was presented.
Abstract: By catalytic hydrogenation of 3-(benzyloxycarbonyl)amino-4H-pyrido[1,2-a]pyridin-4-ones 28 and 29, and azino[1,2-x]pyrimidin-4-ones 32–35, 41, and 42, partial saturation of the heterocyclic systems and removal of the benzyloxycarbonyl moiety was observed to give 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2 a]pyridin-4-ones 30 and 31, and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones 36–39, 43, and 44 in high yields. The methods represent a simple two step synthesis, starting from heterocyclic α-amino compounds and methyl (Z)-2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate followed by catalytic hydrogenation.
TL;DR: In this article, a ring switching transformation of (S)-3-[(dimethylamino)methylidene]-5-(methoxycarbonyl)tetrahydrofuran-2-one (4) with 2-pyridineacetic acid derivatives (5, 7) and 2-aminopyridines (8, 9) afforded the corresponding 3-(4-oxo-4H-quinolizinyl-3)-(1,2-a]pyrimidinyl-1)-2-hydroxypropanoates (
Abstract: A one-step ‘ring switching’ transformation of (S)-3-[(dimethylamino)methylidene]-5-(methoxycarbonyl)tetrahydrofuran-2-one (4) with 2-pyridineacetic acid derivatives (5–7) and 2-aminopyridines (8, 9) afforded the corresponding 3-(4-oxo-4H-quinolizinyl-3)- (15–17) and 3-(4-oxo-4H-pyridino[1,2-a]pyrimidinyl-3)-2-hydroxypropanoates (18, 19), respectively.
TL;DR: Alkyl 2]-2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates 3 and 4 were transformed with C-and N-nucleophiles into β-heteroaryl-α,β-didehydro-α-amino acid derivatives as mentioned in this paper.
Abstract: Alkyl 2-[2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates 3 and 4 were transformed with C-and N-nucleophiles into β-heteroaryl-α,β-didehydro-α-amino acid derivatives 13-16, substituted 3-amino-4H-quinolizin-4-one 17, 2H,5H-benzo[b]pyran-2,5-dione 18 and 19, 2H,5H-pyrano[4,3-b]pyran-2,5-dione 20, 2H,5H-pyrano[3,2-c]benzo[b]pyran-2,5-dione 21, 2H-1-benzopyran-2-one 22 and 24, pyrido[l,2-a]pyrimidin-4-one 31–34 and 39 derivatives, and N-heteroaryl-1H-imidazole-4-carboxylates 37 and 38.
TL;DR: In this paper, a simple stereoselective synthesis of 2Z and 2Z, 1′E alkyl 3-acyloxy-2-(2,2-disubstituted ethenyl) aminopropenoates 4 from alkyyl 2-(2.2, 2, 2-dimethylaminopro-enoates) amino-3-dimethyl) was presented in 12-91% yield.
Abstract: A simple stereoselective synthesis of 2Z and 2Z,1′E alkyl 3-acyloxy-2-(2,2-disubstituted ethenyl) aminopropenoates 4 from alkyl 2-(2,2-disubstituted ethenyl)amino-3-dimethylaminopropenoates 1 in 12–91% yield is presented.