A novel reaction of 6-amino-uracils and isatins

Tetrahedron

Volumn 64, Issue 30-31, 2008, Pages 7307-7311

  Dabiri, Minoo ^a   Azimi, Seyyedeh Cobra ^a   Khavasi, Hamid Reza ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Isatine; Spiro compound; Spiro pyrimidoquinoline 5,5 pyrrolopyrimidine ; Uracil

Indexed keywords

1,1' DIMETHYL 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1' DIMETHYL 7 BROMO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1' DIMETHYL 7 NITRO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1',10 TRIMETHYL 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1',3,3' TETRAMETHYL 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1',3,3' TETRAMETHYL 7 BROMO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 1,1',3,3' TETRAMETHYL 7 NITRO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 10 METHYL 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 10 METHYL 2,2' BIS(METHYLTHIO) 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 2,2' BIS(METHYLTHIO) 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 2,2' BIS(METHYLTHIO) 7 NITRO 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 3 (4 AMINO 1 METHYL 2 (METHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 3 HYDROXY 5 NITROINDOLIN 2 ONE; 3 (4 AMINO 1 METHYL 2 (METHYLTHIO) 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 5 BROMO 3 HYDROXYINDOLIN 2 ONE; 3,3' 10 TRIMETHYL 2,2' BIS(METHYLTHIO) 7 NITRO 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 3,3' DIMETHYL 2,2' BIS(METHYLTHIO) 7 NITRO 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 7 BROMO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; 7 BROMO 2,2' BIS(METHYLTHIO) 7 NITRO 3H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 4,4',6'(3'H,7'H,10H) TRIONE; 7 NITRO 1H SPIRO[PYRIMIDO[4,5 B]QUINOLINE 5,5' PYRROLO[2,3 D]PYRIMIDINE] 2,2',4,4',6'(1'H,3H,3'H,7'H,10H) PENTAONE; ISATIN DERIVATIVE; PYRIMIDINE DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 45449119266     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.063     Document Type: Article

References (21)

1. Bojaroki J.T., Mokrooz J.L., Barton H.J., and Paluchewska M.H. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 38 (1985), Academic, San Diego, CA 229
2. Shaw G. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 3 (1984), Pergamon, Oxford 57
3. Agrawal A., and Chauhan P.M.S. Tetrahedron Lett. 46 (2005) 1345 and references cited therein
4. Sannigrahi M. Tetrahedron 55 (1999) 9007
5. Heathcock C.H., Graham S.L., Pirrung M.C., Plavac F., and White C.T. Spirocyclic Systems. In: Simon J. (Ed). The Total Synthesis of Natural Products Vol. 5 (1983), John Wiley and Sons, New York, NY 264
6. Srivastav N., Mittal A., and Kumar A. J. Chem. Soc., Chem. Commun. (1992) 493
7. James D.M., Kunze H.B., and Faulkner D.J. J. Nat. Prod. 54 (1991) 1137
8. Kobayashi J., Tsuda M., Agemi K., Shigemiri H., Ishibashi M., Sasaki T., and Mikami Y. Tetrahedron 47 (1991) 6617
9. Rewcastle G.W., Bridges A.J., Fry D.W., Rubin J.R., and Denny W.A. J. Med. Chem. 40 (1997) 1820
10. Gready J.E., McKinlay C., and Gebauer M.G. Eur. J. Med. Chem. 38 (2003) 719
11. Tenser R.B., Gaydos A., and Hay K.A. Antimicrob. Agents Chemother. 45 (2001) 3657
12. Ram V.J., Goel A., Sarkhel S., and Maulik P.R. Bioorg. Med. Chem. 10 (2002) 1275
13. Bazgir A., Seyyedhamzeh M., Yasaei Z., and Mirzaei P. Tetrahedron Lett. 48 (2007) 8790
14. Sayyafi M., Seyyedhamzeh M., Khavasi H.R., and Bazgir A. Tetrahedron 64 (2008) 2375
15. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. J. Heterocycl. Chem. 44 (2007) 1009
16. Dabiri M., Azimi S.C., Arvin-Nezhad H., and Bazgir A. Heterocycles 75 (2008) 87
17. Dabiri M., Delbari A.S., and Bazgir A. Synlett (2007) 821
18. Dabiri M., Arvin-Nezhad H., Khavasi H.R., and Bazgir A. Tetrahedron 63 (2007) 1770
19. Dabiri M., Delbari A.S., and Bazgir A. Heterocycles 71 (2007) 543
20. 2 values to final R1=0.0762, wR2=0.1832, and S=1.099 with 338 parameters using 5208 independent reflections (θ range=1.94-29.26°). Hydrogen atoms were located from expected geometry and were not refined. Crystallographic data for 3i have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to The Director, CCDC 672180, Union Road, Cambridge CB2 1EZ, UK. Fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.
21. X-STEP32 Version 1.07b, X-ray Structure Evaluation Package (2000), Stoe & Cie, Darmstadt, Germany