Aryl-Fused Nitrogen Heterocycles by a Tandem Reduction−Michael Addition Reaction

Bunce, Richard A.; Herron, Derrick M.; Ackerman, M.L.

doi:10.1021/jo991899+

Cited by 50 publications

(30 citation statements)

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“…Over the past several years, we have described a number of tandem reaction approaches to nitrogen heterocycles initiated by dissolving metal reduction of nitroarenes [1]. In this project, we sought to extend this strategy to the synthesis of 2,3‐dihydro‐4(1 H )‐quinolinone as well as several (±)‐2‐aryl‐2,3‐dihydro‐4(1 H )‐quinolinones by reductive cyclization of 1‐(2‐nitrophenyl)‐2‐propen‐1‐one derivatives.…”

Section: Introductionmentioning

confidence: 99%

(±)‐2‐Aryl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem reduction–Michael addition reaction

Bunce

Nammalwar

2011

Journal of Heterocyclic Chem

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An efficient synthesis of (±)‐2‐aryl‐2,3‐dihydro‐4(1H)‐quinolinones has been developed from chalcones prepared from 2′‐nitroacetophenone and a series of substituted benzaldehydes. The cyclization sequence is initiated by reduction of the nitro group under dissolving metal conditions using iron powder in concentrated hydrochloric acid. Milder conditions, using acetic acid or acetic acid–phosphoric acid as the reaction medium, were less satisfactory. Procedural details as well as a mechanistic discussion and reaction optimization studies are presented. J. Heterocyclic Chem., (2011).

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Section: Introductionmentioning

confidence: 99%

(±)‐2‐Aryl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem reduction–Michael addition reaction

Bunce

Nammalwar

2011

Journal of Heterocyclic Chem

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“…Earlier work from our laboratory studied a tandem reduction-Michael addition variant of this reaction as a route to the synthesis of 1,2,3,4-tetrahydroquinoline-2-acetic esters [3], and we have recently used this reaction to synthesize 1,2,3,9-tetrahydro-4H-carbazol-4-one [4]. In this investigation, we sought to expand the scope of the tandem reduction-Michael sequence to access functionalized linear-fused tricyclic systems.…”

Section: Introductionmentioning

confidence: 99%

Divergent reactivity in tandem reduction–Michael ring closures of five‐ and six‐membered cyclic enones

Bunce

Nammalwar

Slaughter

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).In this study, methyl (AE)-1-(2-nitrobenzyl)-4-oxo-2-cyclohexene-1-carboxylate and methyl (AE)-(2-nitrobenzyl)-4-oxo-2-cyclopentene-1-carboxylate were prepared and subjected to reductive cyclization under dissolving metal conditions. The two reactants showed divergent behavior with the six-ring substrate reacting at the ester carbonyl and the five-ring substrate closing on the enone double bond. The difference in reactivity is attributed to the conformational flexibility, relative reactivity, and steric environment of C4-substituted six-and five-membered cyclic enones.

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“…However, only few 2,3-dihydro-3-substituted-1,4-benzoxazine derivatives, especially 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives, have been described in the literature [40][41][42][43][44][45]. Jiao et al [46] have reported the synthesis of 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives and the finding of their biological activities in controlling HUVEC apoptosis and A549 cell growth.…”

Section: 4-benzodioxanes and Bioisosteres Of The Non-aromatic Ringmentioning

confidence: 99%

Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds

Cruz‐López¹,

Núñez²,

Conejo‐García³

et al. 2011

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The 2,3-dihydro-1,4-benzodioxin ring system is present in a large number of structures of therapeutic agents possessing important biological activities. Some of them are antihypertensive agents. Others are involved in nervous breakdown and schizophrenia or represent an attractive therapeutic target for the treatment of glaucoma. The 2,3-dihydro-1,4-benzodioxin core has also been developed for the synthesis of inhibitors of 5-lipoxygenase and accordingly, these 2,3-dihydro-1,4-benzodioxins are useful for the treatment of inflammatory diseases such as asthma and arthritis. The synthesis and reactivity of several bioisosteres of the non-aromatic ring will be discussed. The occurrence of the 2,3-dihydro-1,4-benzodioxin structure in various naturally abundant compounds is also known. The total synthesis of angustureine (a novel 1,2,3,4-tetrahydroquinoline alkaloid with a n-pentyl side chain at position 2) will be presented. The bioisosteric replacement of benzene by pyridine in compounds containing the 2-substituted-2,3-dihydro-1,4-benzodioxin core has yielded derivatives of biological interest in diverse therapeutic areas such as central nervous system and cardiovascular diseases. These promising results have prompted interest in the area of 1,4-dioxino-[2,3-b]pyridine analogues. Several modifications on both the aromatic and the non-aromatic rings will be reviewed, including several transformations of the new heterocycles, such as the Smiles rearrangement. Moreover, the enantiomers of 2-and 3-hydroxymethyl-2,3-dihydro-1,4-dioxino-[2,3-b]pyridines, important chiral building blocks for the preparation of several biologically active compounds, have been synthesized. We have made an attempt to take into account the largest possible number of original papers, including our research and others. Publications of the last eleven years are included in this review.

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Aryl-Fused Nitrogen Heterocycles by a Tandem Reduction−Michael Addition Reaction

Cited by 50 publications

References 23 publications

(±)‐2‐Aryl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem reduction–Michael addition reaction

(±)‐2‐Aryl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem reduction–Michael addition reaction

Divergent reactivity in tandem reduction–Michael ring closures of five‐ and six‐membered cyclic enones

Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds

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