Study of reactions between 1,2-diaza-1,3-butadienes and N,N'-diaryl- or N,N'-dialkylthioureas

Tetrahedron

Volumn 55, Issue 47, 1999, Pages 13423-13444

  Attanasi, Orazio A ^a   Filippone, Paolino ^a   Foresti, Elisabetta ^b   Guidi, Barbara ^a   Santeusanio, Stefania ^a  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

1,2 Diaza 1,3 butadienes; Addition reactions; Heterocycles; Hydrazones; Thioureas

Indexed keywords

1,3 BUTADIENE DERIVATIVE; HYDRAZONE DERIVATIVE; THIAZOLE DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

THIA;

EID: 0033585132     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00827-3     Document Type: Article

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23. Gilchrist, T. L.; Sanchez Romero, O. A.; Wasson, R. C. J. Chem. Soc., Perkin Trans. 1 1989, 353; Ferguson, G.; Lough, A. J.; Mackay, D.; Weeratunga, G. J. Chem. Soc., Perkin Trans. 1 1991, 3361; Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Molina, M. M.; Palacios, J. C.; Sánchez, J. B. Tetrahedron Lett. 1991, 32, 2513; Clarke, S. J.; Gilchrist, T. L.; Lemos, A.; Roberts, T. G. Tetrahedron 1991, 47, 5615; Banert, K.; Hagedorn, M. Tetrahedron Lett. 1992, 33, 7331; Gilchrist, T. L.; Lemos, A. J. Chem. Soc., Perkin Trans. 1 1993, 1391; Schantl, J. G.; Kählig, H.; Prean, M. Heterocycles 1994, 37, 1873; Baccolini, G.; Orsolan, G.; Mezzina, E. Tetrahedron Lett. 1995, 36, 447; Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Sánchez, J. B. Tetrahedron:asymmetry 1995, 6, 945; South, M. S.; Jakuboski, T. L. Tetrahedron Lett. 1995, 36, 5703; South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. Tetrahedron Lett. 1996, 37, 1351; Bozzini, S.; Felluga, F.; Nardin, G.; Pizzioli, A.; Pitacco, G.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1996, 1961; Baccolini, G.; Todesco, P. E.; Dalpozzo, R.; De Nino, A. Gazz. Chim. Ital. 1996, 126, 271; Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 5315 and the references cited therein.
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25. Gilchrist, T. L.; Sanchez Romero, O. A.; Wasson, R. C. J. Chem. Soc., Perkin Trans. 1 1989, 353; Ferguson, G.; Lough, A. J.; Mackay, D.; Weeratunga, G. J. Chem. Soc., Perkin Trans. 1 1991, 3361; Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Molina, M. M.; Palacios, J. C.; Sánchez, J. B. Tetrahedron Lett. 1991, 32, 2513; Clarke, S. J.; Gilchrist, T. L.; Lemos, A.; Roberts, T. G. Tetrahedron 1991, 47, 5615; Banert, K.; Hagedorn, M. Tetrahedron Lett. 1992, 33, 7331; Gilchrist, T. L.; Lemos, A. J. Chem. Soc., Perkin Trans. 1 1993, 1391; Schantl, J. G.; Kählig, H.; Prean, M. Heterocycles 1994, 37, 1873; Baccolini, G.; Orsolan, G.; Mezzina, E. Tetrahedron Lett. 1995, 36, 447; Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Sánchez, J. B. Tetrahedron:asymmetry 1995, 6, 945; South, M. S.; Jakuboski, T. L. Tetrahedron Lett. 1995, 36, 5703; South, M. S.; Jakuboski, T. L.; Westmeyer, M. D.; Dukesherer, D. R. Tetrahedron Lett. 1996, 37, 1351; Bozzini, S.; Felluga, F.; Nardin, G.; Pizzioli, A.; Pitacco, G.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1996, 1961; Baccolini, G.; Todesco, P. E.; Dalpozzo, R.; De Nino, A. Gazz. Chim. Ital. 1996, 126, 271; Caposcialli, N.; Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1998, 54, 5315 and the references cited therein.
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49. Thiazole and its derivatives, in the Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
50. Thiazole and its derivatives, in The Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
51. Thiazole and its derivatives, in The Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
52. Thiazole and its derivatives, in The Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
53. Thiazole and its derivatives, in The Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
54. Thiazole and its derivatives, in The Chemistry of Heterocyclic Compounds; Metzger, J. V. Ed.; John Wiley & Sons: New York, 1979; Heterocyclic Chemistry, Vol. 1-4; Suschitzky, H.; Meth-Cohn, O. Eds.; Royal Society of Chemistry: London, 1978-1985; Katritzky, A. R. Handbook of Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Rodd's Chemistry of Carbon Compounds; Coffey, S.; Ansell Elsevier, M. F. Eds.; Elsevier: Oxford, 1986; Progress in Heterocyclic Chemistry, Vol. 1-7; Suschitzky, H.; Scriven, E. F. V. Eds.; Pergamon Press: Oxford, 1989-1995; Advances in Heterocyclic Chemistry; Katritzky, A.R. Ed.; Academic Press: New York, 1963-1994; Liebscher, J. in 1,3-Thiazoles in Hetarenes III, Vol. E8B S. 1-598, Houben-Weyl; G. Thieme Verlag: Stuttgart, New York, 1994; Progress in Heterocyclic Chemistry, Vol. 8; Suschitzky, H.; Gribble, G. W.Eds.; Pergamon Press: Oxford, 1996; Progress in Heterocyclic Chemistry, Vol. 9; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon Press: Oxford, 1997; Dondoni, A.; Merino, P. Thiazoles, Vol. 3, Chapt. 6; Shinkai, I. Ed.; in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Pergamon-Elsevier Science: Amsterdam, 1996 and the references cited therein; Cirrincione, G.; Almerico, A. M.; Aiello, E.; Dattolo, G. Pyrroles Part Two: The Synthesis, Reactivity, and Physical Properties of Substituted Pyrroles, Chapt. 3, Aminopyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1992, p. 299; Bean, G. P. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrolering, Vol. 48, Chapt. 2, The synthesis of 1H-Pyrroles; Jones, R. A. Ed.; in The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1990; pp. 107, 208, 218.
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