Construction of previously inaccessible 2-amino-4-benzyl substituted oxazoles

Lindsey, Christopher C.; O'Boyle, Brendan M.; Mercede, Stephanie J.; Pettus, Thomas R. R.

doi:10.1016/j.tetlet.2003.11.046

Cited by 17 publications

(9 citation statements)

References 11 publications

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“…[39] In method B, the cyanation of 2-iodobenzylamine (4 a) was performed by following a literature procedure that describes the efficient cyanation of benzylamine. [40] Although one might suggest that the strong conjugation of the nitrogen doublet in N-(2-iodobenzyl)cyanamide (7) could slow down the acylation reaction in the second step, previous works made us believe it could occur. [41] Indeed, not only were cyanamides 6 g, 6 k, and 6 l obtained in much improved yields by this method but it also afforded new structures such as N-disubstituted benzoylcyanamides 6 p and 6 q (36 and 84 %), N-furanoyl-and N-thiophenoylcyanamides 6 t and 6 u (73 and 74 %), and N-vinylcyanamides 6 r and 6 s (74 and 54 %).…”

Section: Resultsmentioning

confidence: 99%

Unprecedented Aromatic Homolytic Substitutions and Cyclization of AmideIminyl Radicals: Experimental and Theoretical Study

Beaume

Courillon

Derat

et al. 2008

Chemistry A European J

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Amide-iminyl radicals are versatile and efficient intermediates in cascade radical cyclizations of N-acylcyanamides. They are easily trapped by alkenes or (hetero-)aromatic rings and cyclize into a series of new heterocyclic compounds which bear a pyrroloquinazoline moiety. As an illustration of the synthetic importance of these compounds, the total synthesis of the natural antitumor compound luotonin A was achieved through a tin-free radical cascade cyclization process. Not only do amide-iminyl radicals lead to new tetracyclic heterocycles but these nitrogen-centered radical species also react in aromatic homolytic substitutions. Indeed, the amide-iminyl radical moiety unprecedentedly displaces methyl, methoxy, and fluorine radicals from an aromatic carbon atom. This seminal reaction in the field of radical chemistry has been developed experimentally and its mechanism has additionally been investigated by a theoretical study.

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Section: Resultsmentioning

confidence: 99%

Unprecedented Aromatic Homolytic Substitutions and Cyclization of AmideIminyl Radicals: Experimental and Theoretical Study

Beaume

Courillon

Derat

et al. 2008

Chemistry A European J

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“…(4-Oxazolinyl)methyl carbonate 45 reacted with arylstannanes in the presence of catalytic Pd 2 (dba) 3 and excess lithium chloride (Scheme 32). 57 However, the catalyst system required 40 mol% palladium loading for an efficient carbon-carbon bond formation.…”

Section: Scheme 27 Cross-coupling Of Benzyl Carbonate With Aryltriflumentioning

confidence: 99%

Catalytic Transformations of Benzylic Carboxylates and Carbonates

Kuwano¹

2009

Synthesis

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Benzylic carboxylates and carbonates react with various molecules in the presence of homogeneous palladium or cobalt catalysts. The catalytic transformations occur at the benzylic carbons of the substrates, affording benzylic substitution products. This review surveys the catalytic reactions using benzylic carboxylates and carbonates as substrates. Furthermore, the related studies on (h 3benzyl)metal complexes are summarized in order to facilitate the understanding and consideration of the catalytic substitution. 1 Introduction 2 Chemistry of the (h 3-Benzyl)metal Complex 2.1 Structure of the (h 3-Benzyl)metal Complex 2.2 Reactivity of the (h 3-Benzyl)metal Complex 3 Catalytic Transformations of Benzylic Esters 3.

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“…The efficient synthesis of cyanamides by treatment of a primary amine with cyanogen bromide and sodium carbonate in diethyl ether was reported for the first time in 1976 by Harrison and co-workers 13 (Scheme 3) and has been widely used and adapted since. 14,15…”

Section: Cyanation Of Aminesmentioning

confidence: 99%

The Cyanamide Moiety, Synthesis and Reactivity

et al. 2012

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The cyanamide moiety provides many opportunities as a building block for the synthesis of nitrogen-containing heterocycles. This review discusses the reported methods for the preparation of alkyl-and N-acylcyanamides and illustrates their reactivity visà-vis nucleophilic additions, cycloadditions, radical chemistry and coordination chemistry. 1 Introduction 2 Biological Relevance of the Cyanamide Moiety 3 Access to Cyanamides 3.1 Cyanation of Amines 3.2 Palladium Catalysis 3.3 Deoxygenation of Isocyanates 3.4 Desulfurization of Thioureas 4 Reactivity of Cyanamides 4.1 Nucleophilic Additions 4.2 Cycloadditions 4.3 Additions to Carbonyl Groups 4.4 Chlorinations and Oxidations with tert-Butyl-N-chlorocyanamide 4.5 Cyanamides as Radical Partners 5 Coordination Chemistry of Cyanamides 6 Conclusion

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Construction of previously inaccessible 2-amino-4-benzyl substituted oxazoles

Cited by 17 publications

References 11 publications

Unprecedented Aromatic Homolytic Substitutions and Cyclization of AmideIminyl Radicals: Experimental and Theoretical Study

Unprecedented Aromatic Homolytic Substitutions and Cyclization of AmideIminyl Radicals: Experimental and Theoretical Study

Catalytic Transformations of Benzylic Carboxylates and Carbonates

The Cyanamide Moiety, Synthesis and Reactivity

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