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We have recently found that the 1,2-addition of alkynyllithium reagents to Fischer aryl carbenes derived from menthol is followed by [1,3]-migration of the pentacarbonyltungsten fragment: Barluenga, J.; Trabanco, A. A.; Flórez, J.; García-Granda, S.; Llorca, M. A. J. Am. Chem. Soc. 1998, 120, 12129.
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0344025138
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note
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A complex mixture was formed from pyrrole imine 6.
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60
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0032510073
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The N-methyl carbazole structure has been recently described to possess a high agonist and antagonist activity as a melatonin receptor: Davies, D. J.; Garratt, P. J.; Tocher, D. A.; Vonhoff, S.; Davies, J.; Teh, M.-T.; Sugden, D. J. Med. Chem. 1998, 41, 451.
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3743100587
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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Merlic, C.A.1
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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For previous [3 + 3] heterocyclizations of Fischer carbene complexes, see: (a) Polo, R.; Moretó, J. M.; Schick, U.; Ricart, S. Organometallics 1998, 17, 2135. (b) Bambal, R. B.; Kemmitt, D. W. J. Organomet. Chem. 1989, 362, C18. (c) Huang, Y.; Lu, X. Tetrahedron Lett. 1987, 28, 6219. (d) Wang, S. L.; Wulff, W. D. J. Am. Chem. Soc. 1990, 112, 4550. (e) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855. (f) Merlic, C. A.; Xu, D.; Nguyen, M. C.; Truong, V. Tetrahedron Lett. 1993, 34, 221. (g) Aumann, R.; Roths, K.; Jasper, B.; Frölich, R. Organometallics 1996, 15, 1257. (h) Aumann, R.; Meyer, A. G.; Frölich, R. J. Am. Chem. Soc. 1996, 118, 10853.
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0344025133
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note
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-1, F(000) = 1176, T = 293(2) K. Final conventional R = 0.074 (ωR2 = 0.1753) for 2745 "observed" reflections and 265 variables, GOF = 1.033.
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72
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0030474145
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(a) Rudler, H.; Audouin, M.; Parlier, A.; Martin-Vaca, B.; Goumont, R.; Durand-Réville, T.; Vaissermann, J. J. Am. Chem. Soc. 1996, 118, 12045.
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0344888077
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note
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On the basis of this proposal, it was realized that ring expansion would occur if an imine derived from 2-aminomethylpyrrole were employed (see below): (matrix presented) Unfortunately, the reaction of the benzaldehyde imine with carbene 3 did not afford the corresponding pyrrolodiazepine, but only decomposition products were formed.
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(a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D.; Rogers, R. D. Organometallics 1990, 9, 3142.
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0344025132
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note
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(b) Unpublished results from our laboratory.
-
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77
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0345319239
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note
-
Regarding the metal there are only minor variations, all related to yields, when shifting from chromium to tungsten complexes. This is in sharp contrast with our previous results in the cyclization reactions of simple 1-azadienes with alkynyl Fischer carbene complexes (see refs 4e and 22).
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