On 1,2‐benzisoxazole‐3‐acetic acid and 3‐methyl‐1,2‐benzisoxazole: a restatement

Casini, G.; Guallieri, Fulvio; Stein, M. L.

doi:10.1002/jhet.5570060302

Cited by 24 publications

(7 citation statements)

References 13 publications

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“…3-Methyl-1,2-benzisoxazole has been prepared according to the procedure described in reference [25]. 2-Methyl-1,3-benzoxazole and 2-methoxycyanobenzene were purchased from Sigma-Aldrich (Milan, Italy).…”

Section: Synthesis Of the Compoundsmentioning

confidence: 99%

Gas phase ion chemistry of the heterocyclic isomers 3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole

Giorgi

Salvini

Ponticelli

2004

J. Am. Soc. Mass Spectrom.

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Different mass spectrometric methods, stable isotope labeling, and theoretical calculations have allowed us to structurally characterize and differentiate the isomeric ion structures produced by the two heteroaromatic isomers 3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole. The low-energy collision induced dissociation spectra of their molecular ions show large differences. Although both of them produce abundant loss of CO, that involves a carbon atom of the benzene ring, the 2-methyl-1,3-benzoxazole also shows abundant [M-CHO](+) ions at m/z 104, the intensity of which is quite low in the case of its isomer 3-methyl-1,2-benzisoxazole. In addition, MS/MS measurements of fragment ions show characteristic differences that allow distinction among the isomers depending on the original arrangement of the atoms in the five-membered ring. Theoretical ab initio calculations have allowed to determine chemico-physical properties of different ions and to propose a rationalization of the decomposition pathways followed by the two benz(is)oxazole isomers.

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Section: Synthesis Of the Compoundsmentioning

confidence: 99%

Gas phase ion chemistry of the heterocyclic isomers 3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole

Giorgi

Salvini

Ponticelli

2004

J. Am. Soc. Mass Spectrom.

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“…Ether (300 ml) was added to the cooled mixture and the solids were filtered and washed with ether. The filter cake was stirred with 500 njl of water, the insoluble portion was filtered, and the filtrate was acidified with concentrated HC1 to precipiate 4.8 g (78%) of 3c: mp 122-124°(reported8 mp 123°); ir (Nujol) 1720 (acyl C=0), 1610 cm"1 (2-pyrone C=0); uv max (95% EtOH) 226 nm sh (e 15,200), 301 (13,300); mass spectrum m/e (rel intensity) 218 (50), 200 (15), 189 (100), 162 (17), 121 (50), 120 (25), 105 (12), 93 (12), 92 (25), 77 (25), 43 (5).…”

Section: Experimental Section7mentioning

confidence: 99%

Base rearrangement of chromone-3-carboxylic esters to 3-acyl-4-hydroxycoumarins

Klutchko¹,

Shavel²,

Strandtmann³

1974

J. Org. Chem.

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“…Several reports are available in the literature for the synthesis of 1,2-benzisoxazole [9][10][11], but not much work has been done for the synthesis of furobenzisoxazole. We report herein the synthesis of some new furobenzisoxazole derivatives from hydroxyfurocoumarin.…”

mentioning

confidence: 99%

Studies on the synthesis of furobenzisoxazole derivatives

Patel

Soman

2009

Chem Heterocycl Comp

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Zonisamide, a 1,2-benzisoxazole derivative, is an important antiepileptic agent available on the market [1,2]. It has a close resemblance to indole and the 1,2-benzisoxazole nucleus can be substituted for the indole nucleus as far as auxin (plant cell growth substance) like activity is concerned [3]. Several 3-substituted 1,2-benzisoxazole derivatives have been reported to show anticonvulsive activity [4]. 1,2-Benzisoxazole phosphoradiamidates as a novel antitumor prodrug via bioreductive activation have been also studied [5]. Flucloxacillin, Oxacillin, Cloxacillin, and Dicloxacillin belong to the class of new isoxazole penicillins in current clinical use [6].Some furobenzisoxazole derivatives are reported to possess hypotensive, uricosuric, and diuretic activities and, hence, are useful as therapeutics for the treatment of hyperuricemia, edema, and hypertension [7,8], which prompted us to synthesize new furobenzisoxazole derivatives. Several reports are available in the literature for the synthesis of 1,2-benzisoxazole [9-11], but not much work has been done for the synthesis of furobenzisoxazole. We report herein the synthesis of some new furobenzisoxazole derivatives from hydroxyfurocoumarin.We have synthesized new hydroxyfurocoumarin, which on Posner reaction [12] with hydroxylamine gave furobenzisoxazole. New derivatives of furobenzisoxazole have been synthesized, and interesting observations have been recorded during the course of studies.As shown in Scheme 1, 1-(6-hydroxy-3-methylbenzofuran-5-yl)ethanone 1 [13] and 1-(4-hydroxy-3-methyl-benzofuran-5-yl)ethanone 2 [13] on reaction with pulverized sodium and diethyl carbonate [14] gave new linear 5-hydroxy-3-methylfuro[3,2-g]chromen-7-one 3 and angular 7-hydroxy-3-methylfuro[3,2-g]chromen-7-one 4 isomers, respectively. The structures of both compounds were confirmed by their 1 H NMR spectra.

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On 1,2‐benzisoxazole‐3‐acetic acid and 3‐methyl‐1,2‐benzisoxazole: a restatement

Cited by 24 publications

References 13 publications

Gas phase ion chemistry of the heterocyclic isomers 3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole

Gas phase ion chemistry of the heterocyclic isomers 3-methyl-1,2-benzisoxazole and 2-methyl-1,3-benzoxazole

Base rearrangement of chromone-3-carboxylic esters to 3-acyl-4-hydroxycoumarins

Studies on the synthesis of furobenzisoxazole derivatives

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