Perspectives on 1,4-Benzodioxins, 1,4-Benzoxazines and their 2,3-Dihydro Derivatives

Achari, Basudeb; Mandal, Sukhendu; Dutta, P. K.; Chowdhury, Chinmay

doi:10.1055/s-2004-834816

Cited by 32 publications

(11 citation statements)

References 39 publications

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“…There are excellent reviews on the chemistry of 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives, such as those of Chowdhury [18], and Sinou [19]. The impressive number of publications that have appeared in this field over the recent years bears testimony to the enormous current interest.…”

Section: Introductionmentioning

confidence: 95%

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

COC

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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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Section: Introductionmentioning

confidence: 95%

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

COC

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“…1,2 Morpholine, an aromatic six-membered heterocyclic compound, is characterized by the presence of both amine and ether functional groups. 3 It is a moderately strong base with a pK a of 8.7, which is widely used as an intermediate in multi-organic syntheses. Furthermore, morpholine enhances molecular potency through molecular interactions with the target protein (kinases) or regulates the pharmacokinetic properties, 4 present in numerous pharmaceutical active compounds, such as antidepressant, 5 anticancer, 6 and anti-inflammatory 7 compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

Morpholine Derivatives in Agrochemical Discovery and Development

Liao

et al. 2023

J. Agric. Food Chem.

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Derivatives of morpholine are biologically active organic compounds with special structures discovered in multiple drugs. As a result of the terminal pharmacophore of action and extraordinary activity, they attracted fair attention with regard to pesticide innovation and development. Analysis of brief structure–activity relationships and the summarization of the characteristics of pesticides containing morpholine fragments with efficient activity are key steps in the development of novel pesticides. This review primarily overviews morpholine compounds with insecticidal, fungicidal, herbicidal, antiviral, and plant growth regulation properties to provide educational insight for the creation of new morpholine-containing compounds.

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“…In this context, 1,4-dibenzoxazinone skeleton is present in a wide number of compounds with biological activities and its functionalization could be significant and interesting for medicinal chemistry. [64][65][66][67][68][69][70] Very recently, Huo described the iron catalyzed sp 3 -C-H functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones [71][72] using as a terminal oxidant TBHP [71] or DDQ [72]. We envisioned that this functionalization could be achieved by a visible-light photochemical process.…”

Section: Introductionmentioning

confidence: 99%

9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2-ones through a Friedel-Crafts Reaction

Rostoll‐Berenguer¹,

Blay²,

Pedro³

et al. 2018

Preprint

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A visible-light photoredox functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones through a Friedel-Crafts reaction with indoles using an inexpensive organophotoredox catalyst is described. The reaction uses a dual catalytic system formed by a photocatalyst simple and cheap, 9,10-phenanthrenedione, and a Lewis acid, Zn(OTf)2. 5W white LEDs are used as visible-light source and oxygen from air as a terminal oxidant, obtaining the corresponding products with good yields. The reaction can be extended to other electron-rich arenes.

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Perspectives on 1,4-Benzodioxins, 1,4-Benzoxazines and their 2,3-Dihydro Derivatives

Cited by 32 publications

References 39 publications

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

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

Morpholine Derivatives in Agrochemical Discovery and Development

9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2-ones through a Friedel-Crafts Reaction

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