N-Acylation in combinatorial chemistry

Katritzky, Alan R.; Suzuki, Kazuyuki; Singh, Sandeep K.

doi:10.3998/ark.5550190.0005.102

Cited by 40 publications

(9 citation statements)

References 49 publications

(62 reference statements)

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“…A coupling reagent needs to be able to cope with this whole portfolio of reactivity. Many reviews on coupling reagents have been published, [8][9][10][11][12][13][14] illustrating their importance in the synthetic armoury of the synthetic chemist, but these reviews have often failed to offer a critical view on the subject making the choice of reagent difficult. An important issue is that many of the coupling reagents reported have not been compared to others, making any real evaluation impossible.…”

Section: Introductionmentioning

confidence: 99%

Amide bond formation: beyond the myth of coupling reagents

2009

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Amide bond formation is a fundamentally important reaction in organic synthesis, and is typically mediated by one of a myriad of so-called coupling reagents. This critical review is focussed on the most recently developed coupling reagents with particular attention paid to the pros and cons of the plethora of "acronym" based reagents. It aims to demystify the process allowing the chemist to make a sensible and educated choice when carrying out an amide coupling reaction (179 references).

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Section: Introductionmentioning

confidence: 99%

Amide bond formation: beyond the myth of coupling reagents

2009

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“…The coupling of compounds 2a and/or 2b with Nphthalyamino acids and N-tosylamino acids viz glycine, DL-alanine and DL-phenylalanine in the presence of N,N′dicyclohexylcarbodiimide (DCC) as the condensing agent 26,27 in a one-step reaction at room temperature, yielded 2-N-(phthalyl-glycyl, DL-alanyl or DL-phenylalanyl)pyrimidines 3a-f and 2-N-(tosyl-glycyl, DL-alanyl or DL-phenylalanyl) pyrimidines 4a-f, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New Peptidyl- and Glycosylpyrimidine Derivatives

Aly

Behalo

2011

Journal of Chemical Research

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A new series of 2-N-(phthalyl-or tosylamino acid)pyrimidines have been synthesised from the coupling of pyrimidine derivatives with phthalyl-or tosylamino acids. Hydrazinolysis of 2-N-phthalyl derivatives afforded unprotected amino acid derivatives. New derivatives of peptidylpyrimidines have been synthesised from the reaction of pyrimidine derivatives with α-amino acids methyl ester hydrochloride viz different routes. Also, new glycosides have been prepared from the reaction of pyrimidine derivatives with α-D-glucopyranosyl bromide. Most of the synthesised compounds showed a significant antimicrobial activity.

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“…Some examples of C-acylation by 1-acylbenzotriazoles 915 are collected in Scheme 151 . Thus, acylation of aromatic rings involves reactions of derivatives 915 with thiophene in the presence of ZnBr 2 or TiCl 4 to give corresponding 2-acylthiophenes 914 in high yield <2004CCA175> . Furan reacts similarly.…”

Section: Reactivity Of Substituents Attached To Ring Nitrogensmentioning

confidence: 99%