Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
          
          https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
        Synthesis  2010(5): 849-857  
DOI: 10.1055/s-0029-1218623
   DOI: 10.1055/s-0029-1218623
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkEfficient One-Pot Synthesis of N-Substituted 2-Aminochromones, Their Benzo-Fused Derivatives, and Diaminobenzodipyrandiones of Two New Structural Classes
Further Information
            
               
                  
                        
                              Received
                              20 October 2009 
                      
Publication Date:
04 January 2010 (online)
            
         
      
   Publication History
Publication Date:
04 January 2010 (online)

Abstract
N-Substituted 2-aminochromones and their benzo-fused derivatives were obtained in high yields by a new one-pot synthesis, starting from the appropriate acetamides, salicylic acid or its benzo-fused derivatives, and phosphoryl chloride. By the same reaction, from suitable dihydroxybenzenedicarboxylic acids, some compounds of two new structural classes, 2,7-diaminobenzo[1,2-b:4,5-b′]dipyran-4,9-diones and 2,8-diamino-4H,6H-benzo[1,2-b:5,4-b′]dipyran-4,6-diones, were synthesized.
Key words
amines - chromones - heterocycles - one-pot synthesis - pyrans
- 1a 
             
            Mazzei M.Balbi A.Roma G.Di Braccio M.Leoncini G.Buzzi E.Maresca M. Eur. J. Med. Chem. 1988, 23: 237Reference Ris Wihthout Link
- 1b 
             
            Morris J.Wishka DG.Lin AH.Humphrey WR.Wiltse AL.Gammill RB.Judge TM.Bisaha SN.Olds NL.Jacob CS.Bergh CL.Cudahy MM.Williams DJ.Nishizawa EE.Thomas EW.Gorman RR.Benjamin CW.Shebuski RJ. J. Med. Chem. 1993, 36: 2026Reference Ris Wihthout Link
- 1c 
             
            Benjamin CW.Lin AH.Morris J.Wishka DG.Gorman RR. J. Pharmacol. Exp. Ther. 1993, 265: 457Reference Ris Wihthout Link
- 1d 
             
            Roma G.Cinone N.Di Braccio M.Grossi G.Leoncini G.Signorello MG.Carotti A. Bioorg. Med. Chem. 2000, 8: 751Reference Ris Wihthout Link
- 2a 
             
            Bonin PD.Singh JP.Gammill RB.Erickson LA. J. Vasc. Res. 1993, 30: 108Reference Ris Wihthout Link
- 2b 
             
            Morris J.Shebuski RJ. Curr. Pharm. Des. 1995, 1: 469Reference Ris Wihthout Link
- 2c 
             
            Roma G.Di Braccio M.Grossi G.Marzano C.Simonato M.Bordin F. Farmaco 1998, 53: 494Reference Ris Wihthout Link
- 2d 
             
            Di Braccio M.Grossi G.Roma G.Marzano C.Baccichetti F.Simonato M.Bordin F. Farmaco 2003, 58: 1083Reference Ris Wihthout Link
- 3a 
             
            Vlahos CJ.Matter WF.Hui KY.Brown RF. J. Biol. Chem. 1994, 269: 5241Reference Ris Wihthout Link
- 3b 
             
            Abbott BM.Thompson PE. Bioorg. Med. Chem. Lett. 2004, 14: 2847Reference Ris Wihthout Link
- 3c 
             
            Leahy JJ.Golding BT.Griffin RJ.Hardcastle JR.Richardson C.Rigoreau L.Smith GCM. Bioorg. Med. Chem. Lett. 2004, 14: 6083Reference Ris Wihthout Link
- 3d 
             
            Griffin RJ.Fontana G.Golding BT.Guiard S.Hardcastle JR.Leahy JJ.Martin N.Richardson C.Rigoreau L.Stockley M.Smith GCM. J. Med. Chem. 2005, 48: 569Reference Ris Wihthout Link
- 4a 
             
            Ermili A.Roma G.Mazzei M.Balbi A.Cuttica A.Passerini N. Farmaco, Ed. Sci. 1974, 29: 225Reference Ris Wihthout Link
- 4b 
             
            Ermili A.Roma G. Gazz. Chim. Ital. 1971, 101: 269Reference Ris Wihthout Link
- 4c 
             
            Ermili A.Roma G.Balbi A. Gazz. Chim. Ital. 1971, 101: 651Reference Ris Wihthout Link
- 4d 
             
            Ermili A.Balbi A.Roma G.Ambrosini A.Passerini N. Farmaco, Ed. Sci. 1976, 31: 627Reference Ris Wihthout Link
- 4e 
             
            Roma G.Vigevani E.Mazzei M.Ermili A.Ambrosini A.Passerini N. Farmaco, Ed. Sci. 1978, 33: 822Reference Ris Wihthout Link
- 5a 
             
            Ermili A.Mazzei M.Roma G.Cacciatore C. Farmaco, Ed. Sci. 1977, 32: 375Reference Ris Wihthout Link
- 5b 
             
            Ermili A.Balbi A.Di Braccio M.Roma G. Farmaco, Ed. Sci. 1977, 32: 713Reference Ris Wihthout Link
- 5c 
             
            Bantick JR.Suschitzky JL. J. Heterocycl. Chem. 1981, 18: 679Reference Ris Wihthout Link
- 5d 
             
            Morris J.Wishka DG.Fang Y. J. Org. Chem. 1992, 57: 6502Reference Ris Wihthout Link
- 5e 
             
            Morris J.Wishka DG.Fang Y. Synth. Commun. 1994, 24: 849Reference Ris Wihthout Link
- 5f 
             
            Morris J.Luke GP.Wishka DG. J. Org. Chem. 1996, 61: 3218Reference Ris Wihthout Link
- 6 
             
            Gore TS.Inamdar PK.Nagarkar PM. Indian J. Chem. 1974, 12: 946
- 7 
             
            Oh C.Yi I.Park KP. J. Heterocycl. Chem. 1994, 31: 841
- 8 
             
            Kaye PT.Ramaite IDI. J. Chem. Res., Synop. 1997, 414
- 9 
             
            Roma G.Di Braccio M.Carrieri A.Grossi G.Leoncini G.Signorello MG.Carotti A. Bioorg. Med. Chem. 2003, 11: 123
 
    