- 3-((Hetera)cyclobutyl)azetidines, "stretched" Analogues of Piperidine, Piperazine, and Morpholine: Advanced Building Blocks for Drug Discovery
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Four 3-((hetera)cyclobutyl)azetidine-based isosteres of piperidine, piperazine, and morpholine were designed and synthesized on up to gram scale. The key step of the synthetic sequence included cyclization of N-protected 2-(azetidin-3-yl)propane-1,3-diol
- Feskov, Illia O.,Chernykh, Anton V.,Kuchkovska, Yuliya O.,Daniliuc, Constantin G.,Kondratov, Ivan S.,Grygorenko, Oleksandr O.
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p. 1363 - 1371
(2019/02/07)
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- Rearrangement of dialkyl-2-(azetidin-3-yl)propane-1,3-dioates-a structural revision
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The rearrangement reaction of dialkyl 2-[1-diphenylmethyl)azetidin-3-yl]propane-1,3-dioates during saponification was studied. Contrary to a previous report postulating the formation of a 4-(hydroxy-methyl)-2-oxo-pyrrolidine-3-carboxylic acid derivative, our analytical data showed that the rearrangement reaction led to a lactone ring. This structural revision is based on elemental analysis, IR and two-dimensional NMR studies.
- Faust, Mark R.,Hoesl, Cornelia E.,Wanner, Klaus T.
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experimental part
p. 2981 - 2988
(2009/05/31)
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- Pyridonecarboxylic acid derivatives substituted by a bicyclic amino group as antibacterials
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This invention relates to a N1 -(halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative represented by the following formula (I): STR1 wherein X1 is a halogen atom or a hydrogen atom; X2 is a halogen atom; R1 is a hydrogen atom, a hydroxyl group, a thiol group, a halogenomethyl group, an amino group, an alkyl group or an alkoxy group which may have a substituent group; R2 is a group represented by the following formula (II): STR2 wherein R3 and R4 are independently a hydrogen atom or an alkyl group and n is an integer of 1 or 2; A is a nitrogen atom or a partial structure of the following formula (III): STR3 wherein X3 is a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group, a halogenomethyl group, an alkoxyl group or a halogenomethoxyl group which may have a substituent group; and R is a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidynyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, a 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxymethyl group or a phenylalkyl group, and provides a heterocyclic compound useful as antibacterial drugs.
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- A Straightforward Synthesis of Azetidin-3-ylacetic Acid
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The preparation of azetidin-3-ylacetic acid from epichlorohydrin via diethyl 2-[1-(diphenylmethyl)azetidin-3-yl] propane-1,3-dioate is described.
- Carruthers, Nicholas I.,Wong, Shing-Chun,Chan, Tze-Ming
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p. 430 - 431
(2007/10/03)
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