Formation of five- and six-membered heterocyclic rings under radical cyclisation conditions

Majumdar, K. C.; Basu, Pradipta Kumar; Mukhopadhyay, P.

doi:10.1016/j.tet.2006.09.049

Cited by 91 publications

(17 citation statements)

References 324 publications

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“…Increasing interest in new synthetic routes to recently isolated quinazoline alkaloids [14] on one hand and the growing abundance of radical cyclizations of five-and six-membered heterocyclic rings [15] on the other hand speak for the seminal aspect of this chemistry.…”

Section: Introductionmentioning

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: Introductionmentioning

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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“…In the last three decades, radical cyclizations have emerged as powerful methods for building heterocyclic structures from unsaturated substrates, 14,15 and these reactions have found a number of direct applications in syntheses of complex natural products. Metathesis is currently the process of choice for the direct functionalization of terminal alkenes or alkynes.…”

Section: Scheme 1 Hanson's Approach To Benzosultams 5 By Sequential Hmentioning

confidence: 99%

Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams

Feuillastre¹,

Pelotier²,

Piva³

2013

Synthesis

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“…For intramolecular Meerwein reactions, compounds of type 1 can serve as attractive test systems for new initiators, reaction conditions, and trapping reagents, which are finally responsible for the substituent Y in the cyclized product 2 (Scheme 1) [16,17].…”

Section: Cyclization To Carbon-carbon Double and Triple Bondsmentioning

confidence: 99%

Modern Developments in Aryl Radical Chemistry

Pratsch

Heinrich

2011

Topics in Current Chemistry

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This review summarizes recent advances in the field of aryl radical chemistry. In particular, modern developments of the well-known Meerwein, Pschorr, and Gomberg-Bachmann reactions are presented along with new applications in natural product syntheses. Among the methods for the generation of aryl radicals, tin hydrides play a predominant role, but more and more attractive and promising alternatives are beginning to emerge.

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Formation of five- and six-membered heterocyclic rings under radical cyclisation conditions

Cited by 91 publications

References 324 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

Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams

Modern Developments in Aryl Radical Chemistry

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