Tert-butyl 2-{1-[2-aryl-4-oxothiazol-5(4h)- ylidene]ethyl}diazene-1- carboxylates: A new class of 1,2-diaza-1,3-butadienes

Heterocycles

Volumn 51, Issue 10, 1999, Pages 2423-2430

  Attanasi, Orazio A ^a   Filippone, Paolino ^a   Guidi, Barbara ^a   Perrulli, Francesca R ^a   Santeusanio, Stefania ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033214674     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8649     Document Type: Article

References (50)

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38. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
39. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
40. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
41. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
42. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
43. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
44. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
45. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
46. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
47. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
48. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
49. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.
50. D. L. Boger, Tetrahedron 1983, 39, 2869; D. L. Boger, Chem. Rev., 1986, 86, 781; D. L. Boger and S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic, San Diego, 1987; T. Kametani and S. Hibino, Adv. Heterocycl. Chem., 1987, 42, 246; D. L. Boger and M. Patel, in Progress in Heterocyclic Chemistry, Vol. 1, p. 31, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1989; S. M. Weinreb and P. M. Scola, Chem. Rev., 1989, 89, 1525; W. Carruthers, Cycloaddition Reactions in Organic Synthesis in Tetrahedron Organic Chemistry Series, Vol. 8, ed. by E. J. Baldwin and P. D. Magnus, Pergamon, Oxford, 1990; F. Fringuelli and A. Taticchi, Dienes in the Diels-Alder Reaction, Interscience, John Wiley & Sons, New York, 1990; S. M. Weinreb, in Comprehensive Organic Synthesis, Vol. 5, p. 401, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; D. L. Boger, in Comprehensive Organic Synthesis, Vol. 5, p. 451, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991; J. Barluenga and M. Tomás, Adv. Heterocycl. Chem. 1993, 57, 1; T. Oh and M. Reilly, Org. Prep. Proced. Int., 1994, 26, 129; H. Waldmann, Synthesis 1994, 535; A. Padwa in Progress in Heterocyclic Chemistry, Vol. 7, p. 21, ed. by H. Suschitzky and E. F. V. Scriven, Pergamon, Oxford, 1995.