The 2,1‐benzisothiazolo[2,3‐<i>b</i>]‐2,1‐benzisothiazole system, synthesis and properties

McKinnon, David M.; Duncan, K. Ann

doi:10.1002/jhet.5570250409

Cited by 8 publications

References 13 publications

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ChemInform Abstract: The 2,1‐Benzisothiazolo(2,3‐b)‐2,1‐benzisothiazole System, Synthesis and Properties.

McKinnon

Duncan

1989

ChemInform

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ChemInform Abstract The o,o'-diaminodiphenylmethanes (I), prepared by conventional methods, undergo cyclization with N-sulfinylmethanesulfonamide (II), forming the benzoisothiazoles (III). These are N-methylated to give the methylamino derivatives (V), together with the benzoisothiazolobenzoisothiazoles (VI). In analogy, treatment of (III) with acetic anhydride (VII) produces the tetracycles (VIII) and the diacetylamino compounds (IX).

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ChemInform Abstract: The 2,1‐Benzisothiazolo(2,3‐b)‐2,1‐benzisothiazole System, Synthesis and Properties.

McKinnon

Duncan

1989

ChemInform

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Selective manipulation of only one of two similar sites within a molecule ‘odin reactions’: Strategic advantage for synthesis and tactics available

Milner

1995

J of Chemical Tech & Biotech

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Approaches used to effect selective reaction at one of two or more similar sites in a molecule are reviewed. The nature of the problem is defined and the strategic advantage to be gained through the use of symmetrical intermediates is outlined early and re‐emphasised throughout the discussion with specific examples of multistage syntheses of important products. The various tactics used to effect site selectivity in a late synthetic step are described in a logical sequence and presented in a form aimed to help in the design of syntheses of unsymmetric products from symmetric intermediates.

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Thienoanellierte 6a?4-Thia-1,6-diazapentalene durch baseninduzierte Dimerisierung von 5-Methyl-isothiazoliumsalzen

et al. 1992

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Thienoanneleted 6aλ4‐Thia‐1,6‐diazapentalenes by Baseinduced Dimerisation of 5‐Methyl‐isothiazolium Salts Isothiazolium salts 2 and 3 are easily available by reaction of (Z/E)‐β‐thiocyanatovinyl aldehydes with primary aliphatic and aromatic amines in acetic acid or with aromatic amine hydrochlorides, respectively. Preparative advantages of this reaction are demonstrated and discussed. Reaction of 3 with secondary amines results in an unexpected formation of 6aλ4‐thia‐1,6‐diazapentalenes 5, a new typ of thiadiazapentalenes anellated with a heterocyclic ring system. The structure of 5 was evidenced by IR, UV, 1H‐, 13C‐n.m.r. spectral data and supported by elemental analysis. By means of 15N‐ and 13C‐n.m.r. spectroscopy the synthesized thiadiazapentalenes were found to be stable towards protonation.

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The 2,1‐benzisothiazolo[2,3‐b]‐2,1‐benzisothiazole system, synthesis and properties

Cited by 8 publications

References 13 publications

ChemInform Abstract: The 2,1‐Benzisothiazolo(2,3‐b)‐2,1‐benzisothiazole System, Synthesis and Properties.

ChemInform Abstract: The 2,1‐Benzisothiazolo(2,3‐b)‐2,1‐benzisothiazole System, Synthesis and Properties.

Selective manipulation of only one of two similar sites within a molecule ‘odin reactions’: Strategic advantage for synthesis and tactics available

Thienoanellierte 6a?4-Thia-1,6-diazapentalene durch baseninduzierte Dimerisierung von 5-Methyl-isothiazoliumsalzen

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