6-Chloro-2(2H)-pyranone: A new 2(2H)-pyranone synthon

Tetrahedron Letters

Volumn 44, Issue 3, 2003, Pages 607-610

  Biagetti, Matteo ^a   Bellina, Fabio ^a   Carpita, Adriano ^a   Rossi, Renzo ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

Hydrogenation; Palladium catalysis; Pyrones; Selectivity; Sonogashira reaction

Indexed keywords

6 CHLORO 2(2H) PYRANONE; ACID; COPPER; KETONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ISOMERISM; PRECURSOR; ROOM TEMPERATURE;

EID: 0037433982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02600-X     Document Type: Article

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18. For leading references on this reaction, see: (a) Sonogashira, M.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470; (b) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 129-160; (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549; (d) Bertus, P.; Pale, P. J. J. Organomet. Chem. 1998, 567, 173-180; (e) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641-8644; (f) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039-2042.;
19. For leading references on this reaction, see: (a) Sonogashira, M.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470; (b) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 129-160; (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549; (d) Bertus, P.; Pale, P. J. J. Organomet. Chem. 1998, 567, 173-180; (e) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641-8644; (f) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039-2042.
20. For leading references on this reaction, see: (a) Sonogashira, M.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470; (b) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 129-160; (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549; (d) Bertus, P.; Pale, P. J. J. Organomet. Chem. 1998, 567, 173-180; (e) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641-8644; (f) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039-2042.
21. For leading references on this reaction, see: (a) Sonogashira, M.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470; (b) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 129-160; (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549; (d) Bertus, P.; Pale, P. J. J. Organomet. Chem. 1998, 567, 173-180; (e) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641-8644; (f) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039-2042.
22. For leading references on this reaction, see: (a) Sonogashira, M.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470; (b) Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 129-160; (c) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp. 521-549; (d) Bertus, P.; Pale, P. J. J. Organomet. Chem. 1998, 567, 173-180; (e) Halbes, U.; Bertus, P.; Pale, P. Tetrahedron Lett. 2001, 42, 8641-8644; (f) Halbes, U.; Pale, P. Tetrahedron Lett. 2002, 43, 2039-2042.
23. 8 mp 27°C).
24. 2NH towards 14, the Sonogashira reaction between 14 and 1-alkynes 16 could not be performed in the presence of this secondary amine.
25. 3): δ 43.9 (2C), 48.0, 77.9, 91.7, 109.8, 116.7, 142.7, 144.5, 160.9 ppm.
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