“…However, in the literature there are no data about the implementation of such possibility. There are nevertheless three reports about the [3+1]-cycloaddition of azomethine ylides, generated from aziridines or 1,2,3-triazolines to isonitriles (Scheme ). − Reaction of aziridines 81 with isocyanides afforded two diastereomeric azetidines 83 , which did not undergo epimerization in CDCl 3 solution. 24 …”
“…In these papers, − the mechanism of cycloaddition and formation of cyclic and acyclic products was discussed in details, but there were no data available on the hydrolysis of 3-iminoazetidines 83 , 87 into azetidin-3-ones.…”
“…The involvement of the azetidine ring in 3-iminoazetidine 173 did not necessarily lead to ring expansion but also produced acyclic unsaturated products, as exemplified for the conversion of 173 into functionalized 2-azabutadienes 176 (Scheme ). , …”
Section: C4 Miscellaneousmentioning
confidence: 99%
“…Oxazolines 88 were not formed as a byproduct in this reaction in contrast to the case of unsymmetri- cally substituted azomethine ylides, generated from 1,2,3-triazolines 84 (Scheme 25). 92 In these papers, [90][91][92] the mechanism of cycloaddition and formation of cyclic and acyclic products was discussed in details, but there were no data available on the hydrolysis of 3-iminoazetidines 83, 87 into azetidin-3-ones.…”
“…The involvement of the azetidine ring in 3-iminoazetidine 173 did not necessarily lead to ring expansion but also produced acyclic unsaturated products, as exemplified for the conversion of 173 into functionalized 2-azabutadienes 176 (Scheme 48). 90,91 These 3-iminoazetidines 177 were also cleaved with hydrazine hydrate at room temperature, forming enaminoesters 180 (Scheme 49). 91 Considering the reactions, presented in the given review, it is clear that the methods for azetidin-3one synthesis are not exhausted.…”
I. Introduction 29 II. The Chemistry of Azetidin-3-ones 29 A. Structural Data 29 B. Synthetic Methods for Azetidin-3-ones 31 B.1. Carbonyl Group Generation in the Azetidine Ring 31 B.2. Intramolecular Cyclization Reactions 34 B.3. 1,3-Dipolar Cycloaddition Reactions 36 C. Chemical Properties of Azetidin-3-ones 37 C.1. Transformations of the Carbonyl Group 37 C.2. Condensation Reactions − Synthesis of 2-Benzylideneazetidin-3-ones 40 C.3. Ring Transformations of Azetidin-3-ones 40 C.4. Miscellaneous 41 III. The Chemistry of Oxetan-3-ones 42 A. Structural Data 42 B. Synthetic Methods for Oxetan-3-ones 43 B.1. Decomposition of Diazoketones 43 B.2. Oxidation Reactions 44 B.3. Intramolecular Displacement Reactions 46 B.4. Miscellaneous 47 C. Chemical Properties of Oxetan-3-ones 48 C.1. Ring Opening and Ring Expansion of Oxetan-3-ones 48 C.2. Transformations of the Carbonyl Group 49 IV. The Chemistry of Thietan-3-ones 50 A. Synthetic Methods for Thietan-3-ones 51 A.1. Synthesis from Acyclic Precursors 51 A.2. Synthesis by Ring Transformations 53 B. Chemical Properties of Thietan-3-ones 54 B.1. Transformations of the Carbonyl Group 55 B.2. Aldol Reactions 56 B.3. Ring Transformations 56 V. Acknowledgments 58 VI. References 58
“…However, in the literature there are no data about the implementation of such possibility. There are nevertheless three reports about the [3+1]-cycloaddition of azomethine ylides, generated from aziridines or 1,2,3-triazolines to isonitriles (Scheme ). − Reaction of aziridines 81 with isocyanides afforded two diastereomeric azetidines 83 , which did not undergo epimerization in CDCl 3 solution. 24 …”
“…In these papers, − the mechanism of cycloaddition and formation of cyclic and acyclic products was discussed in details, but there were no data available on the hydrolysis of 3-iminoazetidines 83 , 87 into azetidin-3-ones.…”
“…The involvement of the azetidine ring in 3-iminoazetidine 173 did not necessarily lead to ring expansion but also produced acyclic unsaturated products, as exemplified for the conversion of 173 into functionalized 2-azabutadienes 176 (Scheme ). , …”
Section: C4 Miscellaneousmentioning
confidence: 99%
“…Oxazolines 88 were not formed as a byproduct in this reaction in contrast to the case of unsymmetri- cally substituted azomethine ylides, generated from 1,2,3-triazolines 84 (Scheme 25). 92 In these papers, [90][91][92] the mechanism of cycloaddition and formation of cyclic and acyclic products was discussed in details, but there were no data available on the hydrolysis of 3-iminoazetidines 83, 87 into azetidin-3-ones.…”
“…The involvement of the azetidine ring in 3-iminoazetidine 173 did not necessarily lead to ring expansion but also produced acyclic unsaturated products, as exemplified for the conversion of 173 into functionalized 2-azabutadienes 176 (Scheme 48). 90,91 These 3-iminoazetidines 177 were also cleaved with hydrazine hydrate at room temperature, forming enaminoesters 180 (Scheme 49). 91 Considering the reactions, presented in the given review, it is clear that the methods for azetidin-3one synthesis are not exhausted.…”
I. Introduction 29 II. The Chemistry of Azetidin-3-ones 29 A. Structural Data 29 B. Synthetic Methods for Azetidin-3-ones 31 B.1. Carbonyl Group Generation in the Azetidine Ring 31 B.2. Intramolecular Cyclization Reactions 34 B.3. 1,3-Dipolar Cycloaddition Reactions 36 C. Chemical Properties of Azetidin-3-ones 37 C.1. Transformations of the Carbonyl Group 37 C.2. Condensation Reactions − Synthesis of 2-Benzylideneazetidin-3-ones 40 C.3. Ring Transformations of Azetidin-3-ones 40 C.4. Miscellaneous 41 III. The Chemistry of Oxetan-3-ones 42 A. Structural Data 42 B. Synthetic Methods for Oxetan-3-ones 43 B.1. Decomposition of Diazoketones 43 B.2. Oxidation Reactions 44 B.3. Intramolecular Displacement Reactions 46 B.4. Miscellaneous 47 C. Chemical Properties of Oxetan-3-ones 48 C.1. Ring Opening and Ring Expansion of Oxetan-3-ones 48 C.2. Transformations of the Carbonyl Group 49 IV. The Chemistry of Thietan-3-ones 50 A. Synthetic Methods for Thietan-3-ones 51 A.1. Synthesis from Acyclic Precursors 51 A.2. Synthesis by Ring Transformations 53 B. Chemical Properties of Thietan-3-ones 54 B.1. Transformations of the Carbonyl Group 55 B.2. Aldol Reactions 56 B.3. Ring Transformations 56 V. Acknowledgments 58 VI. References 58
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