Pericyclic transformations at the periphery of chromen-4-one (=4H-1-benzopyran-4-one): An unusual preference for a 1,5-shift of allylic moieties over the ene reaction

Helvetica Chimica Acta

Volumn 86, Issue 1, 2003, Pages 169-180

  Singh, Gurmit ^a   Singh, Gurpinder ^a   Ishar, Mohan Paul S ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; REACTION KINETICS;

INTRAMOLECULAR CYCLIZATIONS;

AROMATIC COMPOUNDS;

(OXOCHROMENYL)PROPENOATE; 1 BENZYL 2H [1]BENZOPYRANO[2,3 B]PYRIDINE 2,5(1H) DIONE DERIVATIVE; 4 OXOCHROMENE 3 CARBOXALDEHYDE; ACRYLIC ACID; ALLYL COMPOUND; CARBONYL DERIVATIVE; CHROMEN 4 ONE; CHROMONE DERIVATIVE; UNCLASSIFIED DRUG; XYLENE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HEATING; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0037284185     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200390008     Document Type: Article

References (35)

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26. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
27. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
28. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
29. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
30. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
31. E. Middelton, C. Kundaswami, in 'The Flavonoids: Advances in Research since 1986', Ed. J. B. Harborne, Chapman & Hall, New York, 1994, p. 619; M. Gill, in 'The Chemistry of Natural Products', 2nd edn., Ed. R. H. Thomson, Blackie, Academic and Professional, Surrey, 1993, p. 60; S. T. Saengchantara, T. W. Waller, Nat. Prod. Rep. 1986, 3, 465; 'Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology 439'; Eds. J. A. Manthy and B. S. Buslig, Plenum, New York, 1998; H. Shitsuka, C. Ohsawa, T. Ohiwa, I. Umeda, Y. Suhana, Antimicrob. Agents Chemother. 1982, 22, 611; 'Annual Reports in Medicinal Chemistry', Ed. D. M. Bailey, Academic Press Inc., New York, 1984, Vol. 19, p. 121; D. J. Bawi, J. W. T. Selway, J. F. Batchelor, M. Tisdale, I. C. Caldcoell, D. A. B. Young, Nature (London) 1981, 22, 369; E. Muller, T. Kalai, J. Jeko, K, Hideg, Synthesis 2000, 1415; G. L. Korkina, I. B. Alfanas'ev, in 'Advances in Pharmacology', Vol. 38, Ed. H. Sies, Academic Press, San Diego, 1997, p. 151; 'Comprehensive Medicinal Chemistry', Eds. C. Hansch, P. G. Sammes, and J. B. Taylor, Pergamon Press, London, 1990, Vol. 6; Y. Deng, J. P. Lee, R. M. Tianosa, J. K. Synder, S. A. E. Etges, D. Kanada, M. P. Synder, J. C. Thoner, J. Nat. Prod. 2000, 63, 1082, and refs. cit. therein; A. Groweiss, J. H. Cardillena, R. M. Boyd, J. Nat. Prod. 2000, 63, 1537; B. Bodo, A. Blond, D. Gunasekar, K. V. Rao, A. G. Damu, B. Jayaparkasam, J. Nat. Prod. 2000, 63, 507; I. A. Kahn, M. A. Avery, C. L. Burandt, D. K. Goins, J. R. Mikell, E. Nash, A. Azadegan, L. A. Walker, J. Nat. Prod. 2000, 63, 1414; T. Kando, K. Oyana, K. Yoshida, Angew. Chem. Int. Ed. 2001, 40, 894; Y. Wang, W. Tan, W. Li, Z. Li, Y. Li, J. Nat. Prod. 2001, 64, 196.
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