Stereoselective synthesis of 2-alkylidene-3-iminoindoles by reaction of 1,1-dianions with oxalic acid bis(imidoyl) chlorides

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3603-3611

  Langer, Peter ^a   Wuckelt, Jörg ^b   Döring, Manfred ^b   Görls, Helmar ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALKYLIDENE 3 IMINOINDOLE DERIVATIVE; ANION; INDOLE DERIVATIVE; NITRILE; OXALIC ACID; SULFONE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0034674455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991701l     Document Type: Article

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38. We refer to the reactive species used as nitrile and sulfone 1,1-dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α-dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
39. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
40. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
41. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
42. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
43. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
44. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
45. We refer to the reactive species used as nitrile and sulfone 1,1- dianions, knowing that they may represent base-associated monolithiated reagents or have a structure different from that of a α,α- dilithiomethane (see Conclusion section). For preparative aspects, see: (a) Kaiser, E. M.; Solter, L. E.; Schwarz, R. A.; Beard, R. D.; Hauser, C. R. J. Am. Chem. Soc. 1971, 93, 4237. (b) Böhme, H.; Stammberger, W. Liebigs Ann. Chem. 1971, 56. (c) Kondo, K.; Tunemoto, D. Tetrahedron Lett. 1975, 17, 1397. (d) Tanaka, K.; Matsui, S.; Kaji, A. Bull. Chem. Soc. Jpn. 1980, 53, 3619. (e) Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3676. (f) Hendrickson, J. J.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1988, 108, 2358. (g) McCrombie, S. W.; Shankar, B. B.; Ganguly, A. K.; Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. Tetrahedron Lett. 1987, 28, 4127. (h) Thomson, M. W.; Handwerker, B. M.; Katz, S. A.; Belser, R. B. J. Org. Chem. 1988, 53, 906, and references therein.
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71. For the structure of α-cyanbenzyllithium in the solid state, see: (a) Boche, G.; Marsch, M.; Harms, K. Angew. Chem. 1986, 98, 373; Angew. Chem., Int. Ed. Engl. 1986, 25, 373. For the structure in solution, see: (b) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (c) Das, R.; Wilkie, C. A. J. Am. Chem. Soc. 1972, 94, 4555.
72. For the structure of α-cyanbenzyllithium in the solid state, see: (a) Boche, G.; Marsch, M.; Harms, K. Angew. Chem. 1986, 98, 373; Angew. Chem., Int. Ed. Engl. 1986, 25, 373. For the structure in solution, see: (b) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (c) Das, R.; Wilkie, C. A. J. Am. Chem. Soc. 1972, 94, 4555.
73. For the structure of α-cyanbenzyllithium in the solid state, see: (a) Boche, G.; Marsch, M.; Harms, K. Angew. Chem. 1986, 98, 373; Angew. Chem., Int. Ed. Engl. 1986, 25, 373. For the structure in solution, see: (b) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (c) Das, R.; Wilkie, C. A. J. Am. Chem. Soc. 1972, 94, 4555.
74. For the structure of α-cyanbenzyllithium in the solid state, see: (a) Boche, G.; Marsch, M.; Harms, K. Angew. Chem. 1986, 98, 373; Angew. Chem., Int. Ed. Engl. 1986, 25, 373. For the structure in solution, see: (b) Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972. (c) Das, R.; Wilkie, C. A. J. Am. Chem. Soc. 1972, 94, 4555.