A new synthesis of sultams from amino alcohols

Lad, Nitin P.; Sharma, Rajiv; Márquez, Víctor E.; Mascarenhas, Malcolm

doi:10.1016/j.tetlet.2013.09.021

Cited by 17 publications

(29 citation statements)

References 11 publications

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“…The organic phase was washed three times with warm water, dried over anhydrous Na 2 SO 4 , and concentrated under reduced pressure. The crude was purified by column chromatography (silica/CH 2 Cl 2 : n ‐hexane 80:20 v/v) allowing to obtain a slight yellow oil …”

Section: Methodsmentioning

confidence: 99%

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Tundidor‐Camba

Araya

González‐Henríquez

et al. 2019

J of Applied Polymer Sci

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Three new diamines derived from epoxide compounds were synthesized. The preparation of diamine monomers implied the reaction between a phenoxyalkyloxirane (alkyl: H, methyl, isopropyl) and bisphenol A, obtaining the respective aliphatic diols, which produced the corresponding dinitro derivatives. Finally, these derivatives were reduced by using palladium/carbon activated as catalyst and hydrazine as a hydrogen source. Then, six oligomeric poly(ether-azomethine)s (PEAzMs) were obtained from a polycondensation reaction between the new diamines and bis(4-formylbiphenyl-4-yl)dialkylsilane (alkyl: methyl, phenyl) with 84-93% yields. The structural characterization of the diamines and PEAzMs was performed by elemental analysis, infrared spectroscopy, and nuclear magnetic resonance spectroscopy ( 1 H, 13 C, and 29 Si). Furthermore, polymers were analyzed by solubility tests, gel permeation chromatography, ultraviolet-visible (UV-vis) spectroscopy, thermogravimetry, and differential scanning calorimetry analysis. The results showed PEAzMs with 2-11 repetitive units, where the design of the monomers allowed to obtain improved solution processability in comparison with previously reported silylated poly(azomethine)s and good thermal stability. Additionally, all samples showed high transparency in the UV-vis region.

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Section: Methodsmentioning

confidence: 99%

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Tundidor‐Camba

Araya

González‐Henríquez

et al. 2019

J of Applied Polymer Sci

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“…In 2013, Mascarenhas and co-workers described an efficient and simple route for the synthesis of five-and six-membered sultams 61.2 from N,O-dimesylated amino alcohols 61.1 through base-mediated S N 2 reactions (Scheme 61). [56] Scheme 61. Base-mediated synthesis of sultams from N,O-dimesylated amino alcohols.…”

Section: Synthesis Of Sultams Through Other Metal-free Methodologiesmentioning

confidence: 99%

“…In 2013, Mascarenhas and co‐workers described an efficient and simple route for the synthesis of five‐ and six‐membered sultams 61.2 from N , O ‐dimesylated amino alcohols 61.1 through base‐mediated S N 2 reactions (Scheme ) …”

Section: Metal‐free Synthesis Of Sultamsmentioning

confidence: 99%

Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

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Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

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“…[58] Mascarenhas et al have described the intramolecular CSICr of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols 87, as a simple method for the synthesis of five-and six-membered sultams 89 (Scheme 20). [59] For primary mesylates 88 the use of lithium acetylide ethylenediamine complex (LAED) as base in DMSO/THF, cleanly gave the cyclic compounds 89A,B in good yields with no traces of elimination products (Scheme 20, eq 1). Conversely, under the same experimental conditions, the use of LAED on secondary mesylates 90 gave the elimination product, an unexpected result that was solved by using n-BuLi/THF as base to afford the corresponding sultams 91 from modest to good yields (Scheme 20, eq 2).…”

Section: Entrymentioning

confidence: 99%

“…It is interesting to note that a simple analysis of a possible alternative retrosynthesis for a compound of type 97 would suggest the known N-benzyl-N-(cyanomethyl) methanesulfonamide (103) (Scheme 22) [61] after CSICr followed Scheme 20. CSICr described by Mascarenhas et al [59] Scheme 21. CSICr reported by Ukrainets et al [49,50] Scheme 22.…”

Section: Entrymentioning

confidence: 99%

Updating the CSIC Reaction (2003–2020)

Dobrydnev

Marco‐Contelles

2021

Eur J Org Chem

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Herein, we have updated the progress and developments of the Carbanion-mediated Sulfonate (or Sulfonamide) Intermolecular Coupling, and Intramolecular Cyclization, abbreviated as CSIC reaction (CSICr), in the last seventeen years from the seminal review published in 2003 in this same Journal. CSICr has proven to be a useful and versatile synthetic tool, efficiently providing a number of open-chain [alkane(sulfonamide)sulfonates] or cylic (sultams and sultones) synthetic intermediates or final products of high value in organic and medicinal chemistry.

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A new synthesis of sultams from amino alcohols

Cited by 17 publications

References 11 publications

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Flexible oligomeric silicon‐containing poly(ether‐azomethine)s obtained from epoxide derivatives. Synthesis and characterization

Sultams: Recent Syntheses and Applications

Updating the CSIC Reaction (2003–2020)

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