Facile method for conversion of 2-(Chloroseleno)benzoyl chloride into 2-substituted 3-hydroxybenzo[b]selenophenes

Synthetic Communications

Volumn 39, Issue 23, 2009, Pages 4271-4281

  Lisiak, Rafal ^a   Mochowski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

2 (chloroseleno)benzoyl chloride; Benzo b selenophenes; Hydrazines; Selenaheterocycles

Indexed keywords

2 (CHLOROSELENO)BENZOYL CHLORIDE; 3 HYDROXYBENZO[B]SELENOPHENE DERIVATIVE; CHLORIDE; NITROGEN; NUCLEOPHILE; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 70350647320     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902898627     Document Type: Article

References (25)

1. Młochowski, J. 1,2-Selenazoles; In Comprehensive Heterocyclic Chemistry III; A. R. Katritzky; C. A. Ramsden; E. V. F. Scriven; R. J. K. Taylor (Eds.); Elsevier: Oxford, 2008; vol.4
2. Shafiee, A.; Ebrahimzadeh, M. A.; Maleki, A. Selenium heterocycles, XLIII: Syntheses of 3,5-diaryl-1,2,4-thiadiazoles and 3,5-diaryl-1,2,4- selenadiazoles. J. Het. Chem. 1999, 36: 901-903
3. Casar, Z.; Leban, I.; Majcen-Le Maréchal, A.; Lorcy, D. Synthesis of diselenadiazafulvalenes and influence of steric strain on their anodic behavior. J. Chem. Soc., Perkin Trans. 1 2002, 1568-1573
4. Geisler, K.; Künzler, A.; Below, H.; Bulka, E.; Pfeiffer, W. D.; Langer, P. Efficient synthesis of 2-unsubstituted 1,3-selenazoles. Synlett. 2003, 08, 1195-1198.
5. Młochowski, J.; Kloc, K.; Lisiak, R.; Potaczek, P.; Wójtowicz, H. Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology. Arkivoc 2007, (vi), 14-46
6. Mugesh, G.; du Mont, W. W.; Sies, H. Chemistry of biologically important synthetic organoselenium compounds. Chem. Rev. 2001, 101, 2125-2180.
7. Młochowski, J.; Giurg, M. Aromaticity of heterocyclic compounds; In Topics in Heterocyclic Chemistry; T. Krygowski, M. Cyranski (Eds.); Springer: Heidelberg, 2008; vol.19, 287-340.
8. Giurg, M.; Said, S. B.; Syper, L.; Młochowski, J. One-pot oxidation of azomethine compounds into arenecarboxylic acids. Synth. Commun. 2001, 31, 3151-3159.
9. Takimiya, K.; Kunugi, Y.; Konda, Y.; Ebata, H.; Toyoshima, Y.; Otsubo, T. 2,7-Diphenyl[1]benzoselenopheno[3,2-b][1]benzoselenophene as a stable organic semiconductor for a high-performance field-effect transistor. J. Am. Chem. Soc. 2006, 128(9), 3044-3050.
10. Ebata, H.; Miyazaki, E.; Yamamoto, T.; Takimiya, K. Synthesis, properties, and structures of benzo[1,2-b:4,5-b0]bis[b]benzothiophene and benzo [1,2-b:4,5-b0]bis[b]benzoselenophene. Org. Lett. 2007, 9(22), 4499-4502.
11. Eicher, T.; Hauptmann, S.; Suschitzky, H.; Suschitzky, J. Chemistry of Heterocycles; Wiley-VCH: Weinheim, Germany, 2003; chap. 5.11, p. 86.
12. Jacobes, A.; Piette, J. Photobiological activity of sulphur and selenium analogues of psoralen. J. Photochem. Photobiol. B 1994, 22, 9-15
13. Jacobes, A.; Piette, J. Synthesis of monosulfur and monoselenium analogues of psor-alen. Tetrahedron 1994, 50, 9315-9324
14. Jacobes, A.; Piette, J. Synthesis of sulfur and selenium analogues of psoralen. Heterocycles 1992, 34, 1119-1132
15. Vedaldi, D.; Affieri, S.; Frank, S.; Dall'Acqua, F.; Jakobs, A.; Piette, J. Sulphur and selenium analogues of psoralen as novel potential photoche-motheraputic agents. Farmaco 1995, 50, 527-536
16. Dobrin, S.; Kaszynski, P.; Waluk, J. Stilbene-like molecules: Sulfur-and selenium-heterosubstituted indolo[3,2-b]indoles. J. Photochem. Photobiol. A 1997, 105, 149-152.
17. Pelkey, E. T. Selenophenes; In Comprehensive Heterocyclic Chemistry III; A. R. Katritzky, C. A. Ramsden, E. V. F. Scriven, R. J. K. Taylor (Eds.); Elsevier: Oxford, 2008; vol.3, chap. 3.13.
18. Magdesieva, N. N.; Vdovin, V. A. Synthesis of benzo[b]selenophene and its methyl homologs. Chem. Heterocycl. Comp. 1970, 6(11), 1375-1379
19. Umezawa, S. Synthese der kondensierten Selenophene durch Einwirkung von Acetylen und Selen. Bull. Chem. Soc. Jpn. 1939, 14, 363-373.
20. Mitra, R. B.; Rabindran, K.; Tilak, B. D. A new synthesis of benzoseleno-phene. Proceed. Ind. Acad. Sci. Sect. A 1954, 8, 263-264.
21. Kasherwani, T.; Worlikar, S. A.; Larock, R. C. Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization. J. Org. Chem. 2006, 17(71), 2307-2312.
22. Kloc, K.; Osajda, M.; Młochowski, J. 2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation-acylation of C-H acids. Chem. Lett. 2001, 30, 826-827.
23. Kloc, K.; Młochowski, J. Selenenylation-acylation of ketones with 2-chloroselenobenzoyl chloride: A novel route to benzo[b]selenophenes. Tetrahedron Lett. 2001, 42, 4899-4902.
24. Młochowski, J.; Gryglewski, R. J.; Inglot, A. D.; Jakubowski, A.; Juchniewicz, L.; Kloc, K. Synthesis and properties of 2-carboxyalkyl-1,2- benzisoselenazol-3(2H)-ones and related organoselenium compounds as a nitric oxide synthase inhibitors and cytokine inducers. Liebigs Ann. Chem. 1996, 1751-1755.
25. Palus, J.; Młochowski, J.; Juchniewicz, L. 2,20- Diselenobisbenzoates and 2,20-diselenobisbenzenesulfonates: New chiral aryl diselenides. Pol. J. Chem. 1998, 8, 1931-1936.