Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction

Cariou, Claire; Clarkson, Guy J.; Shipman, Michael

doi:10.1021/jo801664g

Cited by 132 publications

(36 citation statements)

References 47 publications

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“…Recently, pyrano [2,3-c]pyrazoles have been synthesized using *Corresponding author. Email: jmkhurana1@yahoo.co.in catalysts like triethyamine (28), Mg/Al hydrotalcite (29), glycine (30), and L-proline in [bmim]BF 4 (31) whereas the synthesis of 2-amino-4H-pyrans has been reported using catalysts like Cu(II)oxymetasilicate (34), ZnO/MgO solid sample containing ZnO nanoparticles (35), silica nanoparticles (36), piperidine (37), magnesium oxide (38), or 1,1,3, 3-tetramethylguanidine (TMG) (39) and also under microwaves exposure (40) in one pot reactions. Though there are many reports on the synthesis of 4H-pyrans and 4H-pyrano [2,3-c]pyrazoles.…”

Section: Introductionmentioning

confidence: 99%

Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions

Khurana

Chaudhary

2012

Green Chemistry Letters and Reviews

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A facile and convenient procedure for the synthesis of 4H-pyrans from aldehydes, malononitrile, and ethyl acetoacetate/acetylacetone and also synthesis of 4H-pyrano[2,3-c]pyrazoles from three-component condensation of aldehydes, malononitrile, and pyrazolone or four-component condensation of aldehydes, malononitrile, ethyl acetoacetate, and hydrazine monohydrate using [bmim]OH as task-specific ionic liquid has been described. The protocol proves to be efficient and environmentally benign in terms of high yields, low reaction times, ease of recovery, and reusability of reaction medium.

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Section: Introductionmentioning

confidence: 99%

Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions

Khurana

Chaudhary

2012

Green Chemistry Letters and Reviews

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“…36 These azomethines reacted with alkoxyketenes, generated from acyl chlorides 33 and Et 3 N, to yield C-3 alkoxy-substituted 2-azetidinones 34.…”

Section: Methodsmentioning

confidence: 99%

Advances in synthesis of monocyclic beta-lactams

Singh¹,

Sudheesh²

2014

Arkivoc

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Recent years have witnessed significant advancement in cycloaddition and cyclization strategies for the synthesis of monocyclic β-lactams. Cycloadditions include the Staudinger's keteneimine cycloaddtions and related reaction. Cyclization reactions are reported to furnish β-lactams through N 1 -C 2 , N 1 -C 4 and C 3 -C 4 bond formations employing substrates like β-amino esters, β-amino alcohols, β-hydroxamate esters, and α-amino diazocarbonyls, etc. Some other strategies are silyl carbonylation reactions, ring-enlargement of aziridines, cleavage of one ring of a bicyclic β-lactam, and functional group transformations on the β-lactam rings. Recently, some multi-component reactions have also been designed. This article reviews the advances made in synthetic approaches to monocyclic β-lactams during last five years.

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“…Thus, Shipman devised a reaction sequence allowing for the preparation of a very diverse array of β-lactams by sequential nucleophilic/electrophilic functionalization of a methylene-aziridine 106, delivering an imine 108 via 107 which is then engaged in a [2+2] Staudinger cycloaddition with a ketene [74]. This sequential, one-pot four-component transformation gives access to β-lactams 109 bearing a quaternary center in good overall yields (46-58%) (Scheme 27).…”

Section: Expansion Into Azetidines and Azetidinonesmentioning

confidence: 99%

Ring Expansions of Nonactivated Aziridines and Azetidines

Couty

David

2015

Topics in Heterocyclic Chemistry

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Ring expansions promoted by ring strain in aziridines and azetidines are reviewed in this chapter, putting emphasis on recent applications from the last decade. This vast subject cannot be surveyed here exhaustively, and the reader will be guided to relevant precedent reviews or key reports. Rather, special attention will be put on selected examples and their mechanistic details, aiming to demonstrate that high selectivity can be reached in these reactions. In this issue, this fastgrowing topic has been divided into two distinct chapters, this one dealing with "nonactivated" aziridines and azetidines. Therefore, the reader will only find here examples involving NH-or N-alkylaziridines and N-azetidines as substrates for ring expansions, while N-acyl, N-carbamoyl, or N-tosyl compounds, defined as "activated" substrates, will be presented in the next chapter. This distinction can appear quite arbitrary at first sight but is amply justified by the great difference in reactivity of these distinct substrates. The first part focuses on the ring expansions of nonactivated aziridines into up to seven-membered rings and is further divided into expansions involving the incorporation of one (or more) heteroatoms, followed by ring expansions involving only incorporation of carbon atoms. The same model is then followed for azetidines.

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Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction

Abstract: 2-Methyleneaziridines can be transformed into a variety of 1,3,4,4-tetrasubstituted beta-lactams in moderate to good yields (46-63%) via a "one-pot" process that brings together four components with the formation of three new intermolecular carbon-carbon bonds.

Cited by 132 publications

References 47 publications

Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions

Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions

Advances in synthesis of monocyclic beta-lactams

Ring Expansions of Nonactivated Aziridines and Azetidines

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