Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI<sub>2</sub>-Mediated Morita−Baylis−Hillman Reaction

Sharma, Vasudha; McLaughlin, Mark L.

doi:10.1021/cc100001e

Cited by 15 publications

(3 citation statements)

References 25 publications

(76 reference statements)

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“…A series of substituted glycine allyl ester derivatives was synthesized as shown in Scheme . Iodoacrylates were prepared via Baylis–Hillman reaction and the alkenes functionalized through either Suzuki or Gilman coupling in good yields . Ester reduction, monosilylation, and condensation with Boc-Gly-OH afforded racemic esters 11a–l .…”

Section: Resultsmentioning

confidence: 99%

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

et al. 2011

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Substituted 4-alkylideneprolines represent a rare class of naturally occurring amino acids with promising biological activities. Lucentamycin A is a cytotoxic, marine-derived tripeptide that harbors a 4-ethylidine-3-methylproline (Emp) residue unique among known peptide natural products. In this paper, we examine the synthesis of Emp and related 4-alkylideneprolines employing a versatile ester enolate-Claisen rearrangement. The scope and selectivity of the key rearrangement reaction are described with a number of diversely substituted glycine ester substrates. Treatment of the allyl esters with excess NaHMDS at ambient temperature gives rise to highly substituted α-allylglycine products with good to excellent diastereoselectivities. Resolution of dipeptide diastereomers and cyclization to form the pyrrolidine rings provide rapid access to stereopure prolyl dipeptides. We have applied this strategy to the synthesis of four Emp-containing isomers of lucentamycin A in pursuit of a definitive stereochemical revision of the natural product. Our studies indicate that the Emp stereogenic centers are not the source of structural misassignment. The current strategy should find broad utility in the synthesis of additional natural product analogues and related 3-alkyl-4-alkylidene prolines.

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Section: Resultsmentioning

confidence: 99%

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

et al. 2011

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“…One of the common approaches is Pinner's pyrimidine synthesis (Eq 1, Scheme a), which involves the reaction of amidines (N−C−N) with 1,3‐dicarbonyl compounds (C−C−C). Synthetic variants of the 1,3‐dicarbonyl compounds have also been employed for the synthesis of pyrimidines, for example the Morita‐Baylis‐Hillman reaction . A second interesting approach involves the conversion of N ‐vinyl or N ‐aryl amides with nitriles to the subsequent pyrimidine or quinazoline (Eq 2, Scheme a).…”

Section: Figurementioning

confidence: 99%

Copper‐Catalyzed One‐pot Synthesis of Pyrimidines from Amides, N,N′‐dimethylformamide dimethylacetal, and Enamines

Cai

Lü

2017

Adv Synth Catal

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A versatile copper catalyzed one-pot synthesis of diversely substituted pyrimidines directly from amides, N,N'-dimethylformamide dimethylacetal (DMFÀDMA) and enamines has been established. The reaction involved the two CÀN bonds and one CÀC bond formation by formal [2 + 1 + 3] annulation approach to pyrimidines. This protocol is based on the use of readily available primary amides, DMFÀDMA and enamines to install diand tri-substituted pyrimidine structure with diverse functionality in one-pot manner, which makes this strategy to be appealing for the medicinal chemistry.

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“…Meanwhile, it takes microwave as its reaction condition, which would give off radiation that is harmful to our health . A recent report described the preparation of 2,5,6‐substitued pyrimidines via MgI 2 ‐mediated MBH reaction . In this report, it involves complex catalysts and some toxic solvents as reaction medium.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of 4‐Naphthylpyrimidin‐2‐amine Derivatives under Solvent‐Free Conditions

Rong

Sheng

et al. 2012

Journal of Heterocyclic Chem

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A simple, efficient, and mild protocol for the synthesis of 4‐naphthylpyrimidin‐2‐amine derivatives under solvent‐free conditions by the reaction of aromatic aldehydes (or 1‐naphthaldehyde), 2‐acetylnaphthalene (or aromatic ketones), guanidine carbonate, and sodium hydroxide was reported. The advantages of this protocol include short reaction time, mild reaction conditions, easy workup, high yields, and environmental friendliness.

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Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI₂-Mediated Morita−Baylis−Hillman Reaction

Cited by 15 publications

References 25 publications

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

Copper‐Catalyzed One‐pot Synthesis of Pyrimidines from Amides, N,N′‐dimethylformamide dimethylacetal, and Enamines

An Efficient Synthesis of 4‐Naphthylpyrimidin‐2‐amine Derivatives under Solvent‐Free Conditions

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Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI2-Mediated Morita−Baylis−Hillman Reaction

Cited by 15 publications

References 25 publications

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

An Ester Enolate–Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A

Copper‐Catalyzed One‐pot Synthesis of Pyrimidines from Amides, N,N′‐dimethylformamide dimethylacetal, and Enamines

An Efficient Synthesis of 4‐Naphthylpyrimidin‐2‐amine Derivatives under Solvent‐Free Conditions

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Efficient Assembly of 2,5,6-Substituted Pyrimidines via MgI₂-Mediated Morita−Baylis−Hillman Reaction