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

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.

cyclizations - heterocycles - lactones - Gewald reaction - coumarins

References

1 Romeo G. Russo F. Caruso A. Cutuli V. Amico-Roxas M. Arzneim.-Forsch.  1998,  48:  167 

2 Pathak US. Gandhi NV. Singh S. Warde RP. Jain KS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1992,  31:  223 

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 

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 

6 Modica M. Santagati M. Guccione S. Russo F. Cagnotto A. Goegan M. Mennini T. Eur. J. Med. Chem.  2000,  35:  1065 

7 El-Kerdawy MM. Yousif MY. El-Emam AA. Moustafa MA. El-Sherbeny MA. Boll. Chim. Farm.  1996,  135:  301 

8 Pathak US. Singh S. Padh J. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1991,  30:  618 

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 

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 

18 Shishoo CJ. Jain KS. J. Heterocycl. Chem.  1992,  29:  883 

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 

20b Wolfbeis OS. Marhold EH. Chem. Ber.  1985,  118:  3664 

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 

20e Fathy NM. Abdel Motti FM. Elgemeie GEH. Arch. Pharm.  1988,  21:  509 

20f Sabnis RW. Kazemi Ghadir J. Rangnekar DW. Phosphorus, Sulfur Silicon Relat. Elem.  1992,  1:  1 

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 

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 

23 Vasylyev MV. Bilokin YV. Branytska OV. Kovalenko SM. Chernykh VP. Heterocycl. Commun.  1999,  5:  241 

24a Kovalenko SN. Bylov IE. Belokon’ Ya. V. Chernykh VP. Chem. Heterocycl. Compd. (Engl. Transl.)  2000,  36:  1026 

24b Zhuravel’ IO. Kovalenko SM. Ivachtchenko AV. Chernykh VP. Shinkarenko PE. J. Heterocycl. Chem.  2004,  41:  517 

24c Kovalenko SM. Bylov IE. Sytnik KM. Chernykh VP. Bilokin YaV. Molecules  2000,  5:  1146 

24d Kovalenko SN. Vasil’ev MV. Sorokina IV. Chernykh VP. Turov AV. Rudnev SA. Chem. Heterocycl. Compd. (Engl. Transl.)  1998,  34:  1412 

24e Kovalenko SN. Chernykh VP. Shkarlat AE. Ukrainets IV. Gridasov VI. Rudnev SA. Chem. Heterocycl. Compd. (Engl. Transl.)  1998,  34:  791 

24f Kovalenko SN. Sytnik KM. Nikitchenko VM. Rusanova SV. Chernykh VP. Porokhnyak AO. Chem. Heterocycl. Compd. (Engl. Transl.)  1999,  35:  167 

24g Kovalenko SN. Zubkov VA. Chernykh VP. Turov AV. Ivkov SM. Chem. Heterocycl. Compd. (Engl. Transl.)  1996,  32:  186 

25 Gewald K. Schinke E. Bottcher H. Chem. Ber.  1966,  99:  94 

26 O’Callaghan CN. McMurry TBH. O’Brien JE. J. Chem. Soc., Perkin Trans. 2  1998,  2:  425 

27 Schiemenz GP. Chem. Ber.  1962,  95:  483 

28 Czerney P. Hartmann H. J. Prakt. Chem.  1981,  323:  691