Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

Hanessian, Stephen; Couture, Claude; Wyss, Heinz

doi:10.1139/v85-593

Cited by 25 publications

(15 citation statements)

References 12 publications

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“…Eventually, we found that diazepanone 21 can be selectively produced, with negligible formation of 22, by employing sulfuryl diimidazole, a seldom used reagent developed by Hanessian as a substitute for the classical Mitsunobu reagent. 24 By using the modified conditions, a library of 12 compounds having the general structure 21 was prepared by varying three diversity inputs including the sulfonyl, aldehyde and isocyanide groups. The only limitation is that aromatic isocyanides cannot be employed in this process.…”

Section: Methodsmentioning

confidence: 99%

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Banfi¹,

Riva²,

Basso³

2009

Synlett

112

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This account summarizes the results of studies carried out by the authors during the last 10 years aimed at expanding the utility of the venerable Passerini and Ugi reactions. Particular emphasis is given to efforts that focus on coupling these processes with post-condensation, intramolecular, aliphatic nucleophilic substitution and acyl nucleophilic substitution reactions. The methodologies developed in these investigations serve as the basis for short sequences for the preparation of a diverse number of interesting drug-like structures.

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Section: Methodsmentioning

confidence: 99%

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Banfi¹,

Riva²,

Basso³

2009

Synlett

112

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“…Thus we chose to employ the combination of sulfonyl diimidazole (SDI) with NaH. This methodology was first introduced by Hanessian . Although it is, surprisingly, seldom employed, it was already demonstrated by us[12b] to be an useful alternative to the classical Mitsunobu conditions.…”

Section: Resultsmentioning

confidence: 99%

Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Diversity‐Oriented Multicomponent Approach

et al. 2018

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Levulinic acid, which is one of the most important renewable building blocks derived from lignocellulosic biomass, has been converted in a diversity‐oriented manner into two families of drug‐like bicyclic nitrogen heterocycles. The methodology, endowed with high step economy and operational simplicity, is based on an Ugi multicomponent reaction, which employs amino alcohols as components, followed by a SN2 cyclization. Noteworthy is the successful synthesis of hexahydro pyrrolodiazepinediones, since the cyclization of the isocyanide‐derived secondary amide onto an alcohol to give a seven‐membered ring was unprecedented. Also enantiopure products have been prepared by using chiral amino alcohols.

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“…Furthermore, the hydroxyl group of N-arylamides, as well as peptide analogues,c an be activatedb yc onversion to an imidazolyl sulfonate. [85] Subsequent base-induced ring closure delivers the desired b-lactams in good yields (63-85 %).…”

Section: N1àc4 Cyclizationmentioning

confidence: 99%

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

et al. 2017

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Due to the emerging resistance against classical β‐lactam‐based antibiotics, a growing number of bacterial infections has become harder to treat. This alarming tendency necessitates continued research on novel antibacterial agents. Many classes of β‐lactam antibiotics are characterized by the presence of the 3‐aminoazetidin‐2‐one core, which resembles the natural substrate of the target penicillin‐binding proteins. In that respect, this Review summarizes the different synthetic pathways toward this key structure for the development of new antibacterial agents. The most extensively applied methods for 3‐amino‐β‐lactam ring formation are discussed, in addition to a few less common strategies. Moreover, approaches to introduce the 3‐amino substituent after ring formation are also covered.

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Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid

Abstract: The imidazolylsulfonate group has been found to be a versatile leaving group in the intramolecular cyclization of p-methoxyphenyl amides and related derivatives of N-substituted L-serine to give the corresponding β-lactams.

Cited by 25 publications

References 12 publications

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes

Bicyclic Heterocycles from Levulinic Acid through a Fast and Operationally Simple Diversity‐Oriented Multicomponent Approach

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

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