New functionalized monocyclic beta-lactams suitable precursors for anhydro 2-azacephams

Brkić, Zinka; Herak, J. J.; Mandić, Zoran; Lukić, Irena; Tomić, Mirjana; Kovačević, Miće

doi:10.1016/s0040-4020(01)80182-4

Cited by 5 publications

(1 citation statement)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…m-CPBA is a common reagent that was used in most cases for this transformation (Scheme 27). [78][79][80][81][82] Other oxidants, i. e., NaIO 4 /RuCl 3 , [82][83][84] KMnO 4 , [85,86] performic [87] or peracetic [88] acids, are also suitable. Since the synthesis of α-C-chiral sulfinamides is much less prone to racemization than that of the corresponding sulfonamides, Liskamp and co-workers used the above oxidation strategy for the preparation of their sulfonamide peptidomimetics (Scheme 28).…”

Section: Synthesis From Sulfinamidesmentioning

confidence: 99%

Bypassing Sulfonyl Halides: Synthesis of Sulfonamides from Other Sulfur‐Containing Building Blocks

Sosunovych,

Vashchenko,

Andriashvili

et al. 2023

The Chemical Record

View full text Add to dashboard Cite

This review disclosed synthetic approaches to sulfonyl amides from non‐sulfonyl halogenated precursors. Known methods were systematized into groups and subgroups according to the type of starting organosulfur compound. Thiols, disulfides, and sulfonamides form a group of S(II)‐containing precursors, which are used in oxidative amination reactions. An important and versatile group for oxidative amination is represented with S(IV)‐containing compounds, i. e., sufinates, sulfinamides, DMSO, N‐sulfinyl‐O‐(tert‐butyl)hydroxylamine, etc. A series of S(VI)‐containing precursors for amination reactions (except sulfonyl halides) include sulfonic acids, sulfonyl azides, thiosulfonates, and sulfones. All approaches are represented with the most prominent examples of the resulting sulfonamides, which could be obtained in high yields mostly via short reaction sequences. Promising electrochemical methods for the preparation of sulfonamides from thiols, disulfides, sulfonamides, sulfinic acid derivatives, and dimethyl sulfoxide under mild and green conditions are also highlighted.

show abstract

Section: Synthesis From Sulfinamidesmentioning

confidence: 99%

Bypassing Sulfonyl Halides: Synthesis of Sulfonamides from Other Sulfur‐Containing Building Blocks

Sosunovych,

Vashchenko,

Andriashvili

et al. 2023

The Chemical Record

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: New Functionalized Monocyclic beta‐Lactams Suitable Precursors for Anhydro 2‐Azacephams.

et al. 1994

View full text Add to dashboard Cite

New Functionalized Monocyclic beta-Lactams Suitable Precursors for Anhydro 2-Azacephams.-New functionalized lactams such as (V) and (XI) as well as (IV) and (X) , which are generated via azetidines of type (III) and (IX), are found to be useful intermediates in the synthesis of new anhydro 2-azacephams like (VI) and (XII). -(BRKIC, Z.; HERAK, J. J.; MANDIC, Z.; LUKIC, I.; TOMIC, M.; KOVACEVIC, M.; Tetrahedron 49 (1993) 43, 9801-9814; PLIVA-Res. Inst., 41000 Zagreb, Croatia; EN)

show abstract

Synthesis, structural characterization and stereocontrolled degradation of 2-azacephams

Herak

Vinković

Mandić

et al. 1994

Tetrahedron: Asymmetry

View full text Add to dashboard Cite

New functionalized monocyclic beta-lactams suitable precursors for anhydro 2-azacephams

Cited by 5 publications

References 7 publications

Bypassing Sulfonyl Halides: Synthesis of Sulfonamides from Other Sulfur‐Containing Building Blocks

Bypassing Sulfonyl Halides: Synthesis of Sulfonamides from Other Sulfur‐Containing Building Blocks

ChemInform Abstract: New Functionalized Monocyclic beta‐Lactams Suitable Precursors for Anhydro 2‐Azacephams.

Synthesis, structural characterization and stereocontrolled degradation of 2-azacephams

Contact Info

Product

Resources

About