Parham-type cycliacylation with Weinreb amides. Application to the synthesis of fused indolizinone systems

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1115-1117

  Ruiz, Javier ^a   Sotomayor, Nuria ^a   Lete, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HALOGEN; INDOLIZINE DERIVATIVE; LITHIUM; PYRROLE DERIVATIVE;

ACYLATION; ARTICLE; CYCLIZATION; MOLECULAR BIOLOGY; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0141853746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034194+     Document Type: Article

References (34)

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16. For a review, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15. For some more recent examples, see, for instance: (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216. (c) Alberola, A.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555. (d) Alberola, A.; Álvaro, R.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 13211. (e) Satyamurthi, N.; Singh, J.; Aidhen, I. S. Synthesis 2000, 375. (f) Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107. (g) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Park, O.-H. J. Org. Chem. 2002, 67, 1691.
17. For a review, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15. For some more recent examples, see, for instance: (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216. (c) Alberola, A.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555. (d) Alberola, A.; Álvaro, R.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 13211. (e) Satyamurthi, N.; Singh, J.; Aidhen, I. S. Synthesis 2000, 375. (f) Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107. (g) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Park, O.-H. J. Org. Chem. 2002, 67, 1691.
18. For a review, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15. For some more recent examples, see, for instance: (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216. (c) Alberola, A.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555. (d) Alberola, A.; Álvaro, R.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 13211. (e) Satyamurthi, N.; Singh, J.; Aidhen, I. S. Synthesis 2000, 375. (f) Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107. (g) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Park, O.-H. J. Org. Chem. 2002, 67, 1691.
19. For a review, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15. For some more recent examples, see, for instance: (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216. (c) Alberola, A.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555. (d) Alberola, A.; Álvaro, R.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 13211. (e) Satyamurthi, N.; Singh, J.; Aidhen, I. S. Synthesis 2000, 375. (f) Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107. (g) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Park, O.-H. J. Org. Chem. 2002, 67, 1691.
20. For a review, see: (a) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15. For some more recent examples, see, for instance: (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1993, 58, 7216. (c) Alberola, A.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555. (d) Alberola, A.; Álvaro, R.; González Ortega, A.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 13211. (e) Satyamurthi, N.; Singh, J.; Aidhen, I. S. Synthesis 2000, 375. (f) Wang, X.-J.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107. (g) Suh, Y.-G.; Jung, J.-K.; Seo, S.-Y.; Min, K.-H.; Shin, D.-Y.; Lee, Y.-S.; Park, O.-H. J. Org. Chem. 2002, 67, 1691.
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27. 2 for cases a-f (Charlton, J. L. ; Alauddin, M. M. J. Org. Chem. 1986, 51, 3490), or with HBr (45%) for case f. For representative experimental procedures and characterization data, see the Supporting Information.
28. 2 for cases a-f (Charlton, J. L. ; Alauddin, M. M. J. Org. Chem. 1986, 51, 3490), or with HBr (45%) for case f. For representative experimental procedures and characterization data, see the Supporting Information.
29. This concept has been invoked to explain the enhancement of metalation in hydrogen-metal, metal-metal (Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356), or halogen-metal exchanges (Beak, P.; Musick, T.; Liu, C.; Cooper, T. ; Gallagher, D. J. J. Org. Chem. 1993, 58, 7330).
30. This concept has been invoked to explain the enhancement of metalation in hydrogen-metal, metal-metal (Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356), or halogen-metal exchanges (Beak, P.; Musick, T.; Liu, C.; Cooper, T. ; Gallagher, D. J. J. Org. Chem. 1993, 58, 7330).
31. Pyrrolo[1, 2-b]isoquinolines have been synthesized by (a) addition of ortho-lithiated benzamides to the carbonyl group of the N-benzylpyrrole-2-carbaldehyde: Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955. (b) Cyclisation of amidyl radicals derived from O-acylhydroxamic acid derivatives: Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Photocyclization of 1-benzyl-1-pyrrolinium salts: Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594. (d) Thieno[3,2-f] indolizinones have been prepared by classical Friedel-Crafts acylation: Decroix, B.; Morel, J. J. Heterocycl. Chem. 1991, 28, 81.
32. Pyrrolo[1, 2-b]isoquinolines have been synthesized by (a) addition of ortho-lithiated benzamides to the carbonyl group of the N-benzylpyrrole-2-carbaldehyde: Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955. (b) Cyclisation of amidyl radicals derived from O-acylhydroxamic acid derivatives: Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Photocyclization of 1-benzyl-1-pyrrolinium salts: Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594. (d) Thieno[3,2-f] indolizinones have been prepared by classical Friedel-Crafts acylation: Decroix, B.; Morel, J. J. Heterocycl. Chem. 1991, 28, 81.
33. Pyrrolo[1, 2-b]isoquinolines have been synthesized by (a) addition of ortho-lithiated benzamides to the carbonyl group of the N-benzylpyrrole-2-carbaldehyde: Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955. (b) Cyclisation of amidyl radicals derived from O-acylhydroxamic acid derivatives: Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Photocyclization of 1-benzyl-1-pyrrolinium salts: Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594. (d) Thieno[3,2-f] indolizinones have been prepared by classical Friedel-Crafts acylation: Decroix, B.; Morel, J. J. Heterocycl. Chem. 1991, 28, 81.
34. Pyrrolo[1, 2-b]isoquinolines have been synthesized by (a) addition of ortho-lithiated benzamides to the carbonyl group of the N-benzylpyrrole-2-carbaldehyde: Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955. (b) Cyclisation of amidyl radicals derived from O-acylhydroxamic acid derivatives: Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441. (c) Photocyclization of 1-benzyl-1-pyrrolinium salts: Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594. (d) Thieno[3,2-f] indolizinones have been prepared by classical Friedel-Crafts acylation: Decroix, B.; Morel, J. J. Heterocycl. Chem. 1991, 28, 81.