Download PDF
Synthesis 2006(5): 847-852  
DOI: 10.1055/s-2006-926333
PAPER
© Georg Thieme Verlag Stuttgart · New York

Recyclization of 2-Imino-2H-1-benzopyrans with Nucleophilic Reagents - Reaction of 2-Iminocoumarin-3-carboxamides with 2-Aminothiophene-3-carboxamides

Sergiy M. Kovalenko*, Sergiy V. Vlasov, Valentin P. Chernykh
National University of Pharmacy, 53 Pushkinska str., Kharkiv 61002, Ukraine
e-Mail: kosn@ic.kharkov.ua;
Further Information

Publication History

Received 26 September 2005
Publication Date:
14 February 2006 (online)

    Permissions and Reprints All articles of this category

Abstract

In the course of our research on the synthesis of coumarins, the interaction of 2-iminocoumarin-3-carboxamides with a series of 2-aminothiophene-3-carboxamides was studied. It was established that the initial products - 2-substituted coumarin-3-carboxamides - can undergo rearrangement to 2-(coumarin-3-yl)thieno[2,3-d]pyrimidin-4-ones by refluxing in DMF.

Key words

cyclizations - heterocycles - lactones - Gewald reaction - coumarins

    References

  • 1 Romeo G. Russo F. Caruso A. Cutuli V. Amico-Roxas M. Arzneim.-Forsch.  1998,  48:  167 
    Google Scholar
  • 2 Pathak US. Gandhi NV. Singh S. Warde RP. Jain KS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1992,  31:  223 
    Google Scholar
  • 3 Cho N. Nara Y. Harada M. Sugo T. Masuda Y. Abe A. Kusumoto K. Itoh Y. Ohtaki T. Watanabe T. Furuya S. Chem. Pharm. Bull.  1998,  46:  1724 
    CrossrefGoogle Scholar
  • 4 Shuichi F, Nobuo C, Tetsuya O, and Toshifumi W. inventors; United States Patent US  6140325.  ; Chem. Abstr. 1997, 126, 238392
  • 5 Ismail MMF. Zahran MA. El-Gaby MSA. Ammar YA. Al-Azhar Bull. Sci.  1999,  10:  41 
    Google Scholar
  • 6 Modica M. Santagati M. Guccione S. Russo F. Cagnotto A. Goegan M. Mennini T. Eur. J. Med. Chem.  2000,  35:  1065 
    CrossrefGoogle Scholar
  • 7 El-Kerdawy MM. Yousif MY. El-Emam AA. Moustafa MA. El-Sherbeny MA. Boll. Chim. Farm.  1996,  135:  301 
    Google Scholar
  • 8 Pathak US. Singh S. Padh J. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1991,  30:  618 
    Google Scholar
  • 9 Kretzschmar E, Laban G, Meisel P, Lohmann D, and Grupe R. inventors; GDR Patent DD  272090.  ; Chem. Abstr. 1990, 112, 216953
  • 10 Mkrtchyan AP. Kazaryan SG. Noravyan AS. Akopyan RA. Dzhagatspanyan IA. Akopyan NE. Akopyan AG. Khim.-Farm. Zh.  1986,  20:  1312 
    Google Scholar
  • 11 Temple DL. inventors; French Patent FR  2401163.  ; Chem. Abstr. 1980, 92, 58803
  • 12 Narr B, and Woitun E. inventors; German Patent DE  2200764.  ; Chem. Abstr. 1973, 79, 92270
  • 13 Furuya S, Choh N, Kato K, and Hinuma S. inventors; United States Patent US  6180792.  ; Chem. Abstr. 1996, 125, 247795
  • 14 Dodic N, Gellibert FJ, and Hunter RN. inventors; Patent WO  2004065392.  ; Chem. Abstr. 2004, 141, 174181
  • 15 Terricabras Belart E, Segarra Matamoros VM, Alvarez-Builla Gomez J, Vaquero Lopez JJ, and Minguez Ortega JM. inventors; Patent WO  2004065391.  ; Chem. Abstr. 2004, 141, 157133
  • 16 Umeda N, Uchida S, and Oshiki K. inventors; Japan Patent JP  2002105082.  ; Chem. Abstr. 2002, 136, 294847
  • 17 Elslager EF. Jacob P. Werbel LM. J. Heterocycl. Chem.  1972,  9:  775 
    CrossrefGoogle Scholar
  • 18 Shishoo CJ. Jain KS. J. Heterocycl. Chem.  1992,  29:  883 
    CrossrefGoogle Scholar
  • 19 Woitun E, and Reuter W. inventors; German Patent DE  2117658.  ; Chem. Abstr. 1973, 78, 16214
  • 20a Bragg DR. Wibberley DG. J. Chem. Soc.  1961,  5074 
    Google Scholar
  • 20b Wolfbeis OS. Marhold EH. Chem. Ber.  1985,  118:  3664 
    Google Scholar
  • 20c Zumstein F, Assmann E, and Koenigsberger R. inventors; GDR DD  1098125. 
  • 20d Matei S. Russu J. Coltea P. Grecu R. Rev. Chim. (Bucharest, Rom.)  1982,  33:  527 
    Google Scholar
  • 20e Fathy NM. Abdel Motti FM. Elgemeie GEH. Arch. Pharm.  1988,  21:  509 
    Google Scholar
  • 20f Sabnis RW. Kazemi Ghadir J. Rangnekar DW. Phosphorus, Sulfur Silicon Relat. Elem.  1992,  1:  1 
    Google Scholar
  • 20g Honna T, Ogawa K, Hashimoto S, and Suzue T. inventors; Japan Patent JP  52077087.  ; Chem. Abstr. 1977, 87, 184494
  • 20h Elnagdi MH. Abdallah SO. Ghoneim KM. Ebeid EM. Kassab KN. J. Chem. Res., Synop.  1997,  2:  44 
    Google Scholar
  • 21 Boehm R, Pech R, Petzold B, Lohmann D, and Laban G. inventors; GDR DD  234269.  ; Chem. Abstr. 1986, 105, 208925
  • 22 Bilokin YV. Vasylyev MV. Branytska OV. Kovalenko SM. Chernykh VP. Tetrahedron  1999,  55:  13757 
    CrossrefGoogle Scholar
  • 23 Vasylyev MV. Bilokin YV. Branytska OV. Kovalenko SM. Chernykh VP. Heterocycl. Commun.  1999,  5:  241 
    Google Scholar
  • 24a Kovalenko SN. Bylov IE. Belokon’ Ya. V. Chernykh VP. Chem. Heterocycl. Compd. (Engl. Transl.)  2000,  36:  1026 
    CrossrefGoogle Scholar
  • 24b Zhuravel’ IO. Kovalenko SM. Ivachtchenko AV. Chernykh VP. Shinkarenko PE. J. Heterocycl. Chem.  2004,  41:  517 
    CrossrefGoogle Scholar
  • 24c Kovalenko SM. Bylov IE. Sytnik KM. Chernykh VP. Bilokin YaV. Molecules  2000,  5:  1146 
    CrossrefGoogle Scholar
  • 24d Kovalenko SN. Vasil’ev MV. Sorokina IV. Chernykh VP. Turov AV. Rudnev SA. Chem. Heterocycl. Compd. (Engl. Transl.)  1998,  34:  1412 
    CrossrefGoogle Scholar
  • 24e Kovalenko SN. Chernykh VP. Shkarlat AE. Ukrainets IV. Gridasov VI. Rudnev SA. Chem. Heterocycl. Compd. (Engl. Transl.)  1998,  34:  791 
    CrossrefGoogle Scholar
  • 24f Kovalenko SN. Sytnik KM. Nikitchenko VM. Rusanova SV. Chernykh VP. Porokhnyak AO. Chem. Heterocycl. Compd. (Engl. Transl.)  1999,  35:  167 
    CrossrefGoogle Scholar
  • 24g Kovalenko SN. Zubkov VA. Chernykh VP. Turov AV. Ivkov SM. Chem. Heterocycl. Compd. (Engl. Transl.)  1996,  32:  186 
    CrossrefGoogle Scholar
  • 25 Gewald K. Schinke E. Bottcher H. Chem. Ber.  1966,  99:  94 
    CrossrefGoogle Scholar
  • 26 O’Callaghan CN. McMurry TBH. O’Brien JE. J. Chem. Soc., Perkin Trans. 2  1998,  2:  425 
    Google Scholar
  • 27 Schiemenz GP. Chem. Ber.  1962,  95:  483 
    CrossrefGoogle Scholar
  • 28 Czerney P. Hartmann H. J. Prakt. Chem.  1981,  323:  691 
    CrossrefGoogle Scholar