Novel mono- and bis(spiro-2-amino-4 H -pyrans): Alum-catalyzed reaction of 4-hydroxycoumarin and malononitrile with isatins, quinones, or ninhydrin

Synthesis

Volumn , Issue 10, 2010, Pages 1731-1735

  Karimi, Ali Reza ^a   Sedaghatpour, Fahime ^a  

^a ARAK UNIVERSITY   (Iran)

Author keywords

4 hydroxycoumarin; Alum KAl(SO4)212H2O ; Spiro 2 amino 4 H pyrans

Indexed keywords

4-HYDROXYCOUMARIN; ACENAPHTHENEQUINONE; CATALYZED REACTIONS; EFFICIENT CATALYSTS; MALONONITRILES; MULTICOMPONENT CONDENSATION; NINHYDRIN; PHENANTHRENEQUINONE;

CONDENSATION; SYNTHESIS (CHEMICAL);

CONDENSATION REACTIONS;

4 HYDROXYCOUMARIN; ACENAPHTHENEQUINONE DERIVATIVE; ALUMINUM POTASSIUM SULFATE; BIS(SPIRO 2 AMINO 4H PYRAN) DERIVATIVE; ISATIN; MALONONITRILE; MONO(SPIRO 2 AMINO 4H PYRAN) DERIVATIVE; NINHYDRIN; PHENANTHRENEQUINONE; PYRAN DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 77952071810     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1219748     Document Type: Article

References (36)

1. Foye W O., Principal di Chemico Farmaceutica Piccin Padova (Italy) 1991 416
2. Singh K, Singh J, Singh H, Tetrahedron 1996 52 14273
3. Wang X S., Shi D Q., Tu S T., Yao C S., Synth. Commun. 2003 33 119
4. Abe Y, Ebara H, Okada S, Akaki R, Horii T, Nakao R, Dyes Pigm. 2002 52 23
5. Glover V, Halket J M., Watkins P J., Clow A, Goodwin B L., Sandler M, J. Neurochem. 1998 51 656
6. Kumar R, Bansal R C., Mahmood A, Biog. Amines 1993 9 281
7. Medvedev A E., Clow A, Sandler M, Glover V, Biochem. Pharmacol. 1996 52 385
8. Bhattacharya S K., Glover V, McIntyre I, Oxenkrug G, Sandler M, Neurosci. Lett. 1982 92 218
9. Bhattacharya S K., Mitra S K., Acharya S B., J.Psychopharmacol. 1991 5 202
10. Sundberg R J., The Chemistry of Indoles Academic Press New York 1996
11. DaSilva J F. M., Garden S J., Pinto A C., J. Braz. Chem. Soc. 2001 12 273
12. Abdel-Rahman A H., Keshk E M., Hanna M A., [nl]El-Bady Sh M., Bioorg. Med. Chem. 2004 12 2483
13. Kornet M J., Thio A P., J. Med. Chem. 1976 19 892
14. Hilton S T., Ho T C., Pljevalijcic G, Jones K, Org. Lett. 2000 2 2639
15. Kumar R S., Rajesh S M., Perumal S, Banerjee D, Yogeeswari P, Sriram D, Euro. J. Med. Chem. 2009 1
16. Rahman A, Silva W S. J., Alvi K A., DeSilva K T. D., Phytochemistry 1987 26 865
17. Rahman A, Qureshi M M., Muzaffar A, DeSilva K T. D., Heterocycles 1988 27 725
18. Harada M, Ozaki Y, Chem. Pharm. Bull. 1978 26 48
19. Yong S R., Ung A T., Pyne S G., Skelton B W., White A H., Tetrahedron 2007 63 1191
20. Marti C, Carreira E M., J. Am. Chem. Soc. 2005 127 11505
21. Feldman K S., Karatjas A G., Org. Lett. 2006 8 4137
22. Elinson M N., Ilovaisky A I., Dorofeev A S., Merkulova V M., Stepanov M O., Miloserdov F M., Ogibin Yu N., Nikishin G I., Tetrahedron 2007 63 10543
23. Wang L.-M, Jiao N, Qiu J, Yu J.-J, Liu [nl]J.-Q, Guo F.-L, Liu Y, Tetrahedron 2010 66 339
24. Zhu S.-L, Jia S.-J, Zhang Y, Tetrahedron 2007 63 9365
25. Dabiri M, Bahramnejad M, Baghbanzadeh M, Tetrahedron 2009 65 9443
26. Karimi A R., Behzadi F, Amini M M., Tetrahedron Lett. 2009 49 5393
27. Karimi A R., Pashazadeh R, Synthesis 2010 437
28. Karimi A R., Alimohammadi Z, Amini M M., Mol. Diver. 2010 in press
29. Azizian J, Mohammadi A A., Karimi A A., Mohammadizadeh M R., J. Org. Chem. 2005 70 350
30. Aderemi B O., Hameed B H., J. Mol. Catal. A: Chem. 2009 370 54
31. Sonar S S., Shelke K F., Kakade G K., Shingate B B., Shingare M S., Chin. Chem. Lett. 2009 20 1042
32. Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi A A., Tetrahedron Lett. 2005 46 6123
33. Dabiri M, Salehi P, Baghbanzadeh M, Bahramnejad M, Monatsh. Chem. 2007 138 1253
34. Azizian J, Mohammadi A A., Karimi A R., Mohammadizadeh M R., J. Mol. Catal. A: Chem. 2006 300 85
35. Karimi A R., Mohammadi A A., Lett. Org. Chem. 2008 5 566
36. Dabiri M, Baghbanzadeh M, Kiani S, Vakilzadeh Y, Monatsh. Chem. 2007 138 997