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Synthesis of Benzisochalcogenol and -azole Derivatives via ortho Metalation of Isophthalamides

  • Berthold Kersting EMAIL logo and Michael DeLion
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 8

The syntheses of benzofused isochalcogenazole derivatives via ortho-lithiation of isophthalamides is reported. N ,N′ -Dialkyl-isophthalamides, C6H4-1,3-(CONHR)2, bearing R = iPr or tBu substituents are readily ortho metalated by using 3.3 equiv. of n-BuLi/TMEDA. The organo lithium compounds react with S, Se, or Te to give 2-chalcogenol-isophthalamides, C6H3 -1,3- (CONHR)2-2-XH (X = S, Se, Te). Oxidation of the chalcogenols affords dichalcogenides under acidic and benzisochalcogenazoles under basic conditions, respectively. The formation of the five-membered heterocycles proceeds by disproportionation of the dichalcogenides. Oxidation of the benzisothiazoles by hydrogen peroxide gives access to substituted sulfin- and sulfonamides.

: Isophthalamides; Metalation; Chalcogen; Insertion; Oxidation
Received: 1999-6-1
Published Online: 2014-6-2
Published in Print: 1999-8-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Darstellung und Eigenschaften von Tetra(n-butyl)ammonium-cis-diacidooxophthalocyaninato( 2-)niobaten(V) und -tantalaten(V); Kristallstruktur von (nBu4N)CIS[Nb(F)2Opc2-]
  2. Metallkomplexe mit biologisch wichtigen Liganden, CXXI [1]. Orthopalladierte Enolate aus N-(Diphenylmethylen)-Schiff-Basen von a-Aminosäureestern als ambivalente 1,3-Dipole in [2+3]-Cycloadditionsreaktionen. Strukturen einer Reihe von Cycloaddukten
  3. Metallkomplexe mit biologisch wichtigen Liganden, CXX [1]. Halbsandwich-Komplexe von Ruthenium(II) und Iridium(III) mit 3-(3-Pyridyl)-D-alaninat
  4. Metallboranate und Boranatometallate, 25. 25Mg-Kernresonanzuntersuchungen an Magnesiumboranaten [1]
  5. Kristallstruktur, Infrarot- und Ramanspektren sowie thermische Zersetzung von Magnesiumtetrahydrogendimesoperiodat, MgH4I2O10 · 6H2O
  6. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)(SCN)], trans-(n-Bu4N)2[ReBr4(NCS)(SCN)] und trans-(n-Bu4N)2[ReBr4(NCSe)(SeCN)]
  7. Serendipitous Formation of the Cyclic Sulfite DIMTH(SO3) by Reaction of DIMTH(OH)2 with SOCl2
  8. Neue Tetraaminophosphonium-Salze durch Anionenaustausch in flüssigem Ammoniak
  9. The Crystal Structure of N,N′-Bis-(1,3-dihydroxy-2-methylprop-2-yl)- pyrazine-2,3-dicarboxamide Semihydrate
  10. β-Diketonates and their Analogs: Stabilization of the Dimeric M2{L}4(D)2 (M = Co, Ni) Core in the Complexes with Dimethyl-N-trichloroacetylamidophosphate {Cl3C(O)NP(O)(OCH3)2}-
  11. Synthesis and Electronic Spectra of Tricarbonylrhenium(I) Chloride Complexes with 9,10-Phenanthrenequinone and 9,10-Phenanthrenequinone Diimine as Acceptor Ligands
  12. Synthesis of Benzisochalcogenol and -azole Derivatives via ortho Metalation of Isophthalamides
  13. Synthesis, Reactions and Spectroscopy of 3-Benzoyl-6-phenylpyridazines of Expected Biological Activity
  14. Imidazole Nucleosides, V. Synthesis of 3′-Fluoro-3′-deoxy-ribofuranosides of 4(5)-Amino-imidazoIe-5(4)carboxamide
  15. Synthetic Potential Inherent in D-Isoascorbic Acid as a Precursor for Pyridazine and Furo[3,2-c]pyridazine Ring Systems with Two Asymmetric Centers
  16. Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, I
  17. Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, II
  18. Die Kristallstruktur von Bis(bromotriphenyl) arsen(V)-hexabromotellurat( IV), [Ph3AsBr]2[TeBr6]
  19. Darstellung und Kristallstruktur von Hexacaesium-hexatelluridodigermanat( III) (Cs6Ge2Te6)
https://doi.org/10.1515/znb-1999-0812

Articles in the same Issue

  1. Darstellung und Eigenschaften von Tetra(n-butyl)ammonium-cis-diacidooxophthalocyaninato( 2-)niobaten(V) und -tantalaten(V); Kristallstruktur von (nBu4N)CIS[Nb(F)2Opc2-]
  2. Metallkomplexe mit biologisch wichtigen Liganden, CXXI [1]. Orthopalladierte Enolate aus N-(Diphenylmethylen)-Schiff-Basen von a-Aminosäureestern als ambivalente 1,3-Dipole in [2+3]-Cycloadditionsreaktionen. Strukturen einer Reihe von Cycloaddukten
  3. Metallkomplexe mit biologisch wichtigen Liganden, CXX [1]. Halbsandwich-Komplexe von Ruthenium(II) und Iridium(III) mit 3-(3-Pyridyl)-D-alaninat
  4. Metallboranate und Boranatometallate, 25. 25Mg-Kernresonanzuntersuchungen an Magnesiumboranaten [1]
  5. Kristallstruktur, Infrarot- und Ramanspektren sowie thermische Zersetzung von Magnesiumtetrahydrogendimesoperiodat, MgH4I2O10 · 6H2O
  6. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von cis-(n-Bu4N)2[ReBr4(NCS)(SCN)], trans-(n-Bu4N)2[ReBr4(NCS)(SCN)] und trans-(n-Bu4N)2[ReBr4(NCSe)(SeCN)]
  7. Serendipitous Formation of the Cyclic Sulfite DIMTH(SO3) by Reaction of DIMTH(OH)2 with SOCl2
  8. Neue Tetraaminophosphonium-Salze durch Anionenaustausch in flüssigem Ammoniak
  9. The Crystal Structure of N,N′-Bis-(1,3-dihydroxy-2-methylprop-2-yl)- pyrazine-2,3-dicarboxamide Semihydrate
  10. β-Diketonates and their Analogs: Stabilization of the Dimeric M2{L}4(D)2 (M = Co, Ni) Core in the Complexes with Dimethyl-N-trichloroacetylamidophosphate {Cl3C(O)NP(O)(OCH3)2}-
  11. Synthesis and Electronic Spectra of Tricarbonylrhenium(I) Chloride Complexes with 9,10-Phenanthrenequinone and 9,10-Phenanthrenequinone Diimine as Acceptor Ligands
  12. Synthesis of Benzisochalcogenol and -azole Derivatives via ortho Metalation of Isophthalamides
  13. Synthesis, Reactions and Spectroscopy of 3-Benzoyl-6-phenylpyridazines of Expected Biological Activity
  14. Imidazole Nucleosides, V. Synthesis of 3′-Fluoro-3′-deoxy-ribofuranosides of 4(5)-Amino-imidazoIe-5(4)carboxamide
  15. Synthetic Potential Inherent in D-Isoascorbic Acid as a Precursor for Pyridazine and Furo[3,2-c]pyridazine Ring Systems with Two Asymmetric Centers
  16. Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, I
  17. Chiral Pool Synthesis of 4a-Substituted Carbocyclic Cyclopentanoid Nucleoside Precursors, II
  18. Die Kristallstruktur von Bis(bromotriphenyl) arsen(V)-hexabromotellurat( IV), [Ph3AsBr]2[TeBr6]
  19. Darstellung und Kristallstruktur von Hexacaesium-hexatelluridodigermanat( III) (Cs6Ge2Te6)
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