Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent:  Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

Gordon, Kirsteen; Balasubramanian, Shankar

doi:10.1021/ol006766l

Cited by 35 publications

(21 citation statements)

References 22 publications

(23 reference statements)

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“…For example, the acylation of Rink amide secondary amines with amino acids possessing bulky side chains was reported to occur in only modest yields (60%) [95]. The authors have reported a new amine linker of this category that is cleaved using ceric [96] ammonium nitrate [Ce(NO 3 ) 6 (NH 4 ) 2 , CAN]. The linker has been designed for the release of secondary amides and, in particular, b-lactams but will have broader application.…”

Section: Solid-phase Techniques For B-lactam Synthesismentioning

confidence: 99%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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Since the discovery of penicillin in 1929, b-lactam antibiotics have been recognized as potentially chemotherapeutic drugs of incomparable effectiveness, conjugating a broad spectrum of activity with very low toxicity. The primary motif azetidin-2-one ring (b-lactam) has been considered as specific pharmacophores and scaffolds. With the advent of combinatorial chemistry and automated parallel synthesis coupled with ample interests from the pharmaceutical industries, recent trends have been driven mostly by adopting solid phase techniques and polymersupported synthesis of b-lactams. The present survey will present an overview of the developments on the polymer-supported and solid phase techniques for the preparation of b-lactam ring or b-lactam containing antibiotics published over the last decade. Both unsubstituted and substitutions with different functional groups at various positions of b-lactams have been synthesized using solid phase technology. However, Wang resin and application of Staudinger [2+2] cycloaddition reaction have remained hitherto the major choice. It may be expected that other solid phase approaches involving different resins would be developed in the coming years.

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Section: Solid-phase Techniques For B-lactam Synthesismentioning

confidence: 99%

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Mandal

Ghosh

Basu

2010

Heterocyclic Scaffolds I

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“…The most challenging of these reactions proved to be the Sn(II) reduction, which has been somewhat variable for the reduction of nitroaromatic molecules on solid phase by a number of groups pursuing other targets. An alternative approach would be to directly load an N-Boc protected 3-iodo-4-aminophenol [Gordon and Balasubramanian, 2001], which would circumvent the need for reduction of the nitro group on solid phase.…”

Section: Intramolecular Heck Reactionmentioning

confidence: 99%

Solid phase chemical technologies for combinatorial chemistry

Balasubramanian

2001

J. Cell. Biochem.

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“…CAN has been widely used in organic reactions which include oxidation, [12][13][14][15][16] oxidative addition, [17][18][19][20][21] photooxidation, 22 nitration, [23][24][25] deprotection, 26,27 graft polymerization, 28,29 etc. Intermediates formed in these reactions may undergo oxidative fragmentation, 30,31 rearrangement, [32][33][34] or C-H, C-C and C-S bond [35][36][37][38] cleavages. Organic sulfides can be oxidized with catalytic amounts of Ce(IV) salts rapidly and selectively to sulfoxides.…”

Section: Introductionmentioning

confidence: 99%

(Anthracen-9-yl)methyl sulfides as a mechanistic probe for chemical as well as photochemical electron-transfer reactions

Gopalakrishnan¹,

Jacob²,

Moideen³

et al. 2015

Arkivoc

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We have examined the intermediacy of sulfur-centred radical cations in the one-electron oxidation of (anthracen-9-yl)methyl sulfides. Reaction of (anthracen-9-yl)methyl sulfides with ceric ammonium nitrate (CAN) gave predominantly nitration and oxidation products along with products arising through sulfur-centred radical cations in minor amounts. Upon irradiation, (anthracen-9-yl)methyl sulfides underwent efficient intramolecular single electron transfer leading to a variety of products arising through the intermediacy of sulfur-centred radical cations.

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Exploring a Benzyloxyaniline Linker Utilizing Ceric Ammonium Nitrate (CAN) as a Cleavage Reagent: Solid-Phase Synthesis of N-Unsubstituted β-Lactams and Secondary Amides

Cited by 35 publications

References 22 publications

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Recent Approaches Toward Solid Phase Synthesis of β-Lactams

Solid phase chemical technologies for combinatorial chemistry

(Anthracen-9-yl)methyl sulfides as a mechanistic probe for chemical as well as photochemical electron-transfer reactions

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