Skip to main content

Advertisement

Log in

A One-Pot Entry to a Novel 3-H-benzo[d]pyrazolo[1,5-b]isothiazole Ring System

  • Published:
Molecular Diversity Aims and scope Submit manuscript

Summary

The phosphorus ylide obtained from the reaction between 2-aminobenzo[d]isothiazol-3-one and dimethyl acetylenedicarboxylate in the presence of triphenylphosphine undergoes a smooth intramolecular Wittig-type reaction to produce, in a one-pot reaction, 3-H-benzo[d]pyrazolo[1,5-b]isothiazole-2,3a-dicarboxylic acid dimethyl ester, a novel functionalized heterocyclic compound.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. La Colla P. and Vicini P., “Composti biciclici di potenziale impiego nelle infezioni da HIV” Brevetto d'invenzione DP 2004 A/02, 22 Marzo 2004.

  2. Vicini, P., Zani, F., Cozzini, P. and Doytchinova, I, Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations, Eur. J. Med. Chem., 37 (2002) 553–564.

    Article  PubMed  CAS  Google Scholar 

  3. Vicini, P., Geronikaki, A., Incerti, M., Busonera, B., Poni, C., Cabras, C. A. and La Colla, P., Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases, Bioorg. Med. Chem., 11 (2003) 4785–4789.

    Article  PubMed  CAS  Google Scholar 

  4. Zani, F., Vicini, P. and Incerti, M., Synthesis and antimicrobial properties of 2-(benzylidene -amino)-benzo[d]isothiazol-3-ones, Eur. J. Med. Chem., 39/2 (2004) 135–140.

    Article  CAS  Google Scholar 

  5. Geronikaki, A., Vicini, P., Incerti, M. and Hadjipavlou-Litina D., Thiazolyl and isothiazolyl azomethine derivatives with antiinflammatory and antioxidant activities. Synthesis, biological evaluation and structure activity relationships study, Arzneim.Forcsh/Drug Res., 9 (2004) 530–537.

    Google Scholar 

  6. Panico, A. M., Vicini, P., Massimo, G., Cardile, V., Gentile, B., Avondo, S., Vittorio, F. and Ronsisvalle, G., Protective effects of benzisothiazolylamidines on IL-1β induced alterations in human articular chondrocyte metabolism, Inflammation, 28 (2004) 231–235.

    Article  PubMed  CAS  Google Scholar 

  7. With the name ‘privileged structure’ is defined a class of molecules capable of binding to multiple receptors with high affinity. For a review see, for example: Douglas, A. H., Gregory, T. B. and Mark, L. S., The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures, Chem. Rev., 103 (2003) 893–930.

  8. Hudson, H. R., Nucleophilic reactions of phosphines, Hantley, F. R., (Ed.) The chemistry of organophosphorus compounds: primary, secondary and tertiary phosphines and heterocyclic organophosphorus (III) compounds, Vol. 1, Wiley: NewYork, 1990, 386–472.

    Google Scholar 

  9. Arduago, A. J. and Stewart, C. A., Low coordinate hypervalent phosphorus, Chem. Rev., 94 (1994) 1215–1237.

    Article  Google Scholar 

  10. Pietrusiewiz, K. M. and Zabloka, M., Preparation of Scalemic P-Chiral Phosphines and Their Derivatives, Chem. Rev., 94 (1994) 1375–1411.

    Article  Google Scholar 

  11. Hughes, A. N., Synthetic application of dimethyl acetylenedicarboxylate in phosphorus heterocyclic chemistry. Heterocycles, 15 (1) (1981) 637–665.

    Article  CAS  Google Scholar 

  12. Yavari, I., Nasiri, F. and Djahaniani, H., Triphenyphosphines catalyzed reaction between 1,3-dicarbonyl compounds and acetylenic esters, Phosphorus, sulfur and silicon and the related elements, 178 (12) (2003) 2627–2638.

    Article  CAS  Google Scholar 

  13. Yavari, I., Adib, M., Jahani-Mogaddan, F. and Sayahi, M. H., A simple synthesis of stable heterocyclic phosphorus ylides derived from NH-acids, Phosphorus, sulfur and silicon, 177 (2002) 545–553.

    Article  CAS  Google Scholar 

  14. Yavari, I., Nourmohammadian F. and Bijanzadeh, H. R., Synthesis of dimethyl 2-(2,4,6-trimethylphenoxy)-3-triphenylphosphino- botanedioate and its application in intramolecular Wittig reactions, Phosphorus, sulfur and silicon, 177 (2002) 1147–1152.

    Article  CAS  Google Scholar 

  15. Yavari, I., Alizadeh, A. and Anari-Abbasinejad, M., Reaction between heterocyclic NH-acids and dibenzoylacetylene in the presence of triphenylphospine. Simple synthesis of 1-(3-furyl)-1H-imidazole derivatives, Tetrahedron Lett., 43 (2002) 9449–9452.

    Article  CAS  Google Scholar 

  16. Yavari, I., Anari-Abbasinejad, M. and Hossaini, Z., Reaction between naphthols and dimethyl acetylenedicarboxylates in the presence of phosphites. Synthesis of stable oxa-2-phosphaphenanthrenes and benzochromene derivatives, Org. Biomol. Chem., 1 (2003) 560–564.

    Article  PubMed  CAS  Google Scholar 

  17. Yavari, I., Alizadeh, A. and Anari-Abbasinejad, M., Efficient synthesis of functionalized 2,5-diihydro-1,2-oxaphospholes, Tetrahedron Lett., 44 (2003) 2877–2879.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Paola Vicini.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vicini, P., Incerti, M., Ferretti, R. et al. A One-Pot Entry to a Novel 3-H-benzo[d]pyrazolo[1,5-b]isothiazole Ring System. Mol Divers 10, 251–253 (2006). https://doi.org/10.1007/s11030-005-9011-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-005-9011-3

Keywords

Navigation