Author
A. Sinur
Bio: A. Sinur is an academic researcher from University of Ljubljana. The author has contributed to research in topics: Reagent & Substitution reaction. The author has an hindex of 2, co-authored 3 publications receiving 31 citations.
Topics: Reagent, Substitution reaction
Papers
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TL;DR: In this paper, a new reagent for the synthesis of hetero-cyclic β-amino-α,β-dehydro amino acid derivatives and some fused heterocyclic systems was obtained from N-2,2-bis(ethoxycarbonyl)vinyl glycinate and N-N-dimethyl-formamide dimethyl acetal.
29 citations
TL;DR: In this article, the C(2) = C(3) double-bond configuration with respect to the benzoyl and (methoxy) (methylthio) methyleneamino groups are turned out of the best plane through the rest of molecule.
Abstract: The compounds ethyl (E)-2-benzoyl-3-(dimethylamino)propenoate, C 14 H 17 NO 36 (I), ethyl (Z)-2-benzoyl-3-[(3nitrophenyl)amino]propenoate, C 18 H 16 N 2 O 5 (II), and methyl (Z)-3-[(4,6-dimethyl-2-pyrimidinyl)amino]-2[(methoxy)(methylthio)methyleneamino]propenoate, C 13 H 18 N 4 O 3 S (III), are propenoates with different substituents at the C(2) = C(3) double bond. C(2) bears benzoyl and ethoxycarbonyl groups in (I) and (II) and (methoxy)(methylthio)methyleneamino and methoxycarbonyl groups in (III), whereas C(3) is substituted with dimethylamino in (I), 3-nitrophenylamino in (II) and 4,6-dimethyl-2-pyrimidinylamino in (III). The configuration with respect to the C(2) = (3) double bond is E in (I) and Z in (II) and (III). Bulky substituents such as the benzoyl and (methoxy) (methylthio) methyleneamino groups are turned out of the best plane through the rest of molecule
2 citations
TL;DR: In this paper, a new reagent for the synthesis of hetero-cyclic β-amino-α,β-dehydro amino acid derivatives and some fused heterocyclic systems was obtained from N-2,2-bis(ethoxycarbonyl)vinyl glycinate and N-N-dimethyl-formamide dimethyl acetal.
Abstract: Ethyl (Z)-2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-dimethylaminopropenoate (5), a new reagent in the synthesis of heteroaryl substituted β-amino- α,β- -dehydro—amino acid derivatives and some fused hetero-cyclic systems, was prepared from ethyl N-2,2-bis(ethoxycarbonyl)vinylglycinate (3) and N,N-dimethyl-formamide dimethyl acetal (4). The substitution of the dimethylamino group in the compound 5 with heterocyclic amines produced ethyl 2-[2,2-bis(ethoxycarbonyl)vinyl]amino-3-heteroarylaminopropenoates 7a-f and, in some instances, [2,2-bis-(ethoxycarbonyl)vinyl]aminoazolo- or -azinopyrimidine derivatives 8g-k.
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430 citations
57 citations
TL;DR: Methyl (Z)-2-acetylamino-3-dimethylaminopropenoate (3) was shown to be a versatile reagent in the synthesis of various heterocyclic systems as discussed by the authors.
40 citations
TL;DR: Methyl 2-(benzyloxycarbonyl)aimno-3-dimemylaminopropenoate (2) was prepared from methyl N-(bensyloxy carbonyl)-glycinate (1) and t-butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-amino compounds 7, 8, 20, 36, 38 and 53-57 in yields better than 80% as discussed by the authors.
38 citations
TL;DR: In this article, the use of enamines as synthons and possible applications of enaminates in heterocyclic synthesis is discussed, with most attention paid to the formation of pyrroles.
Abstract: Publisher Summary There is a rich synthetic potential for enamines in heterocyclic synthesis. This chapter reviews the use of enamines as synthons and possible applications of enamines in heterocyclic synthesis. The formation of small rings, five-membered rings, and six-membered rings is also focused in the chapter. In comparison with small-ring heterocycles, the formation of five-membered rings from enamines is quite numerous, with most attention paid to the formation of pyrroles. The synthesis of furan, thiophene derivatives, azoles, and other sulfur as well as phosphorous containing five-membered rings are discussed in the chapter. The synthesis of pyridine derivatives, substituted pyrans, thiopyrans, dioxanes, and seven as well as eight-membered rings are also provided in the chapter. The order of presentation is based on the type of heterocyclic compound formed by these ring-closure reactions. The chapter focuses on the pathways of the cyclization reactions involving enamines and their mechanisms. Enamines can react as electrophiles or nucleophiles and as new partners in cycloaddition reactions. Various derivatives of nitrogen-, oxygen-, and sulfur-containing heterocycles are prepared and these are of interest as starting materials for additional syntheses. They represent potential synthons for the development of various new directions in organic chemistry.
30 citations