The Kinetics and Mechanism of the Decomposition of 2,4-Dihydroxy-1,4-benzoxazin-3-one.

Bredenberg, Johan B-son; Honkanen, Erkki; Virtanen, Artturi I.; Motzfeldt, K.; Theander, Olof; Flood, Hugh D.

doi:10.3891/acta.chem.scand.16-0135

Cited by 61 publications

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“…1) to BOA also has been reported as quantitative (4). However, since this result was obtained only by UV spectroscopy, the conversion of DIBOA to BOA may require reexamination if it is to be used analytically for measurement of DIBOA.…”

Section: Discussionmentioning

confidence: 89%

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Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions

Woodward¹,

Corcuera²,

Helgeson³

et al. 1978

Plant Physiol.

140

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Cyclic hydroxanc acids present in some species of Gramineae have been reported to be Important In resbtace of these plnts to fngi aNd insects. Since The amount of DIMBOA5 (Fig. 1) and its glucoside may total more than 1% of the dry wt of corn plants (14,16). In aqueous solutions near neutral pH, free DIMBOA has been reported to decompose quantitatively to MBOA and formic acid (28,29). This facile decomposition of DIMBOA to MBOA has been used for the measurement of DIMBOA content ofcorn by isotopic dilution (15), spectrofluorometry (3), and IR analysis (22). By each method, MBOA is the compound actually measured, and 100% conversion of DIMBOA to MBOA is assumed.

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Section: Discussionmentioning

confidence: 89%

“…The kinetics of the decomposition of DIBOA, an analog of DIMBOA, has been examined in aqueous solutions (4). However, ethanol was used as the solvent in the only kinetic study of the decomposition of DIMBOA (27).…”

mentioning

confidence: 99%

Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions

Woodward¹,

Corcuera²,

Helgeson³

et al. 1978

Plant Physiol.

140

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confidence: 99%

Benzazoles. 4. Synthesis and chemical reactions of 6-chlorosulfonylbenzoxazolin-2-ones

Karimova¹,

Dushamov

Kuryazov

et al. 2011

Chem Heterocycl Comp

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The great interest in derivatives of benzoxazolin-2-ones is explained by their wide range of biological activity [2][3][4][5][6]. Stability of a series of cultures to fungal diseases depends on the content of some compounds of this group [2][3][4]. Benzoxazolin-2-one was isolated from sprouting rye [5], while 6-methoxy-and 6,7-dimethoxybenzoxazolin-2-ones were isolated from the roots of Coix Lacryma jobi [4] and Scaporia dulcus [6].In the continuation of investigations on electrophilic substitution in a series of nitrogen-containing heterocyclic compounds [7][8][9][10], in this work we have studied the chlorosulfonylation of benzoxazolin-2-one (1a) and its 3-methyl derivative 1b, and also some chemical reactions of the products obtained, which allowed the synthesis of a series of new derivatives of compounds 1a,b.The formation of the corresponding 6-chlorosulfonylbenzoxazolin-2-ones from the reaction the benzoxazolin-2-ones 1a,b with chlorosulfonic acid did not depend on the ratio of the reagents. However, isolation of the intermediate sulfoacids 2a,b was not successful, probably due to the easy nucleophilic substitution of the hydroxyl group by the chorine atom connected with the increased positive charge on the sulfur atom of the sulfogroups. The highest yield of products 2a,b (75 and 78% respectively) were achieved by using a fivefold excess of chlorosulfonic acid.

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“…b-Nitroacrylates are an emerging class of functionalized nitroalkenes that show high chemical versatility since they have been employed as strategic starting materials for the preparation of a variety of fine chemicals [8] and natural products. [9] Benzoxazines constitute a class of compounds of important biological interest, [10] in particular, 1,4-benzA C H T U N G T R E N N U N G oxazin-2-one structures, usually synthesized by the reaction between o-aminophenols with a-keto esters [11][12][13] or alkyl propriolates, [14] are of great interest due to both their photochemical activity [11,15] and their presence in many important products such as cephalandole alkaloids, [16] analogues of squamocin, [17] drugs (such as psoralen plus UVA). [13] A plausible mechanism of our reaction consists in a domino process in which four different transformations are involved: (i) hetero-Michael addition of the amine functionality to nitroolefins giving the intermediates 3, (ii) intramolecular transesterification with formation of 4, (iii) elimination of a molecule of nitrous acid affording the intermediates 5, and (iv) [1,3]-proton shift with the formation of target products 6, as previously reported in the literature.…”

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confidence: 99%

Preparation of 2H‐1,4‐Benzoxazin‐2‐one Derivatives under Heterogeneous Conditions via Domino Process

et al. 2009

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The Kinetics and Mechanism of the Decomposition of 2,4-Dihydroxy-1,4-benzoxazin-3-one.

Cited by 61 publications

References 0 publications

Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions

Decomposition of 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one in Aqueous Solutions

Benzazoles. 4. Synthesis and chemical reactions of 6-chlorosulfonylbenzoxazolin-2-ones

Preparation of 2H‐1,4‐Benzoxazin‐2‐one Derivatives under Heterogeneous Conditions via Domino Process

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