Isothiazoles and their Benzo Derivatives

Pain, D. L.; Peart, B; Wooldridge, K. R. H.

doi:10.1016/b978-008096519-2.00085-0

Cited by 33 publications

(18 citation statements)

References 234 publications

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“…The structure (bond lengths, bond angles, and substituent orientation) is consistent with those reported for molecules that contain DMAD, isothiazole or adamantyl moieties. However, the carbon-sulphur bonds (C3-S1: 1.690(4) A, reported average: 1.720 A) and the carbon4arbon (C1 and C2: 1.429(6) A, reported average 1.454 A) bonds are significantly shorter than the related bonds in previously reported isothiazole structures (16). These observations may be due to the influence of n bond delocalisation to the methyl carboxylate moieties.…”

Section: Fig 2 Ortep View Of Ch-cnsc(c(o)och~)c(c(o)och~)mentioning

confidence: 71%

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The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

Bridson¹,

Copp²,

Schriver³

et al. 1994

Can. J. Chem.

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. Adamantyl-1,3,4-oxathiazol-2-one has been prepared for the first time and from it 1-adamantyl nitrile sulphide has been generated. Characterisation data are presented, including the X-Ray crystal structure of the oxathiazolone. (Crystal data for C,,H,,NO,S: monoclinic, space group F'2,/c, a = 11.334(2) A, b = 7.344(1) A, c = 14.373(2) A, P = 107.74(1)", V = 1139.5(3) AS, Z = 4, R = 0.042). The planar heterocyclic ring is similar to structures observed in the gas phase for other oxathiazolone derivatives. The nitrile sulphide was reacted with dimethyl-acetylene dicarboxylate in situ to give an isothiazole derivative. On a prtparC l'adamantyl-l,3,4-oxathiazol-2-one pour la premikre fois et on l'a utilise pour gCnCrer la sulfure de l-adamantyl nitrile. On prCsente les donntes ayant semi ?i sa caractCrisation, y compris la structure de l'oxathiazolone determinee par diffraction des rayons X. Les donntes cristallines pour C,,H,,NO,S sont les suivantes: cristaux monocliniques, groupe d'espace [Traduit par la Rtdaction]

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Section: Fig 2 Ortep View Of Ch-cnsc(c(o)och~)c(c(o)och~)mentioning

confidence: 71%

“…Most known nitrile sulphides have been reacted with DMAD and give the expected isothiazole heterocycles in varying yields. This is an important route to an industrially significant family of heterocycles which are used in the pesticide and pharmaceutical industries (16).…”

Section: Cycloaddition Reaction Of Adamantyl Nitrile Sulphide Withmentioning

confidence: 99%

The preparation of 1,2,3,5-dithiadiazolium chlorides from the reaction of nitrile sulphides with thiazyl chloride

Bridson¹,

Copp²,

Schriver³

et al. 1994

Can. J. Chem.

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“…A closer look at the values in Table 1 showed that the most deshielded methyl carbon signals (6 20.0-22.6 ppm) were observed for the 4-or 4,6-substituted compounds whereas the 4-unsubstituted derivatives appeared at lower frequencies (6 16. 8 …”

Section: Resultsmentioning

confidence: 99%

Carbon‐13 NMR studies on azolopyridines. 3—the isothiazolopyridine systems

Chimichi¹,

Cosimelli²,

Tedeschi³

et al. 1994

Magnetic Reson in Chemistry

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“…The most widely known derivative, saccharin (4), the first noncarbohydrate sweetening agent discovered in 1879, is 300-500 times as sweet as sucrose [16]. Saccharin (4) is manufactured commercially by the cyclization of orthosubstituted benzenesulfonamides with strong bases [17].…”

Section: Introductionmentioning

confidence: 99%