Porphyrins with exocyclic rings. Part 12. Synthesis of meso,β-butano- and meso,β-pentanoporphyrins from cycloalka[b]pyrroles

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6299-6310

  Bastian, Jolie A ^a   Lash, Timothy D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 BUTANO 13,17 DIETHYL 2,7,8,12,18 PENTAMETHYLPORPHYRIN; 3,5 BUTANO 7,13,17 TRIETHYL 2,8,12,18 TETRAMETHYLPORPHYRIN; 3,5 PENTANO 13,17 DIETHYL 2,7,8,12,18 PENTAMETHYLPORPHYRIN; 3,5 PENTANO 7,13,17 TRIETHYL 2,8,12,18 TETRAMETHYLPORPHYRIN; EXOCYCLIC DOUBLE BOND; MESOPORPHYRIN; PORPHYRIN; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032482285     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00327-5     Document Type: Article

References (56)

1. 1. Part 11: Novak, B.H.; Lash, T.D. J. Org. Chem. 1998, submitted.
2. 2. Results presented, in part, at the 84th Annual Meeting of the Illinois State Academy of Science, University of Illinois at Chicago, Chicago, Illinois, Oct. 1991 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1991, Suppl. to Vol. 84, 42); 203rd National Meeting of the American Chemical Society, San Francisco, California, April 1992 (Abstract: Bastian, J.A.; Lash, T.D., Book of Abstracts, CHED 98); 85th Annual Meeting of the Illinois State Academy of Science, Springfield, Illinois, Oct. 1992 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1992, Suppl. to Vol. 85, 45).
3. 2. Results presented, in part, at the 84th Annual Meeting of the Illinois State Academy of Science, University of Illinois at Chicago, Chicago, Illinois, Oct. 1991 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1991, Suppl. to Vol. 84, 42); 203rd National Meeting of the American Chemical Society, San Francisco, California, April 1992 (Abstract: Bastian, J.A.; Lash, T.D., Book of Abstracts, CHED 98); 85th Annual Meeting of the Illinois State Academy of Science, Springfield, Illinois, Oct. 1992 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1992, Suppl. to Vol. 85, 45).
4. 2. Results presented, in part, at the 84th Annual Meeting of the Illinois State Academy of Science, University of Illinois at Chicago, Chicago, Illinois, Oct. 1991 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1991, Suppl. to Vol. 84, 42); 203rd National Meeting of the American Chemical Society, San Francisco, California, April 1992 (Abstract: Bastian, J.A.; Lash, T.D., Book of Abstracts, CHED 98); 85th Annual Meeting of the Illinois State Academy of Science, Springfield, Illinois, Oct. 1992 (Abstract: Bastian, J.A.; Lash, T.D. Trans. III. St. Acad. Sci. 1992, Suppl. to Vol. 85, 45).
5. 3. Baker, E.W.; Palmer, S.E. In The Porphyrins, Ed. Dolphin, D.; 1978, Vol. 1, pp 486-552; Academic Press, New York. Callot, H.J. In The Chlorophylls, Scheer, H., Ed.; CRC Press, Boca Raton, 1991, pp 339-364.
6. 3. Baker, E.W.; Palmer, S.E. In The Porphyrins, Ed. Dolphin, D.; 1978, Vol. 1, pp 486-552; Academic Press, New York. Callot, H.J. In The Chlorophylls, Scheer, H., Ed.; CRC Press, Boca Raton, 1991, pp 339-364.
7. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
8. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
9. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
10. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
11. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
12. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
13. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
14. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
15. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
16. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
17. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
18. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
19. 4. Fischer, H.; Hofmann, H.J. Justus Liebigs Ann. Chem. 1935, 517, 274; Sugihara, J.M.; McGee, L.R. J. Org. Chem. 1957, 22, 795; Baker, E.W.; Corwin, A.H.; Klesper, E.; Wei, P.E. J. Org. Chem. 1968, 33, 3144; Flaugh, M.E.; Rapoport, H. J. Am. Chem. Soc. 1968, 90, 6877; Chaudry, I.A.; Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1980, 33, 1095; Evstigneeva, R.P. Pure Appl. Chem. 1981, 53,1129; Pomonarev, G.V.; Shul'ga, A.M.; Subock, V.P. Dokl. Akad. Nauk SSSR 1981, 259, 1121; Pomonarev, G.V. Khim. Geterotsikl. Soedin. 1981, 1693; Smith, K.M.; Langry, K.C.; Minnetian, O.M. J. Org. Chem. 1984, 49, 4602; Bauder, C.; Ocampo, R.; Callot, H.J. Synlett 1990, 335; ibid., Tetrahedron Lett. 1991, 32, 2537; Clezy, P.S.; Mirza, A.H.; Prashar, J.K. Aust. J. Chem. 1990, 43, 857; Clezy, P.S.; Van Phuc, L.; Prashar, J.K. ibid. 1991, 44, 1061.
20. 5. Clezy, P.S.; Prashar, J.K. Aust. J. Chem. 1990, 43, 825; Clezy, P.S.; Jenie, U.; Prashar, J.K. ibid., 839.
21. 5. Clezy, P.S.; Prashar, J.K. Aust. J. Chem. 1990, 43, 825; Clezy, P.S.; Jenie, U.; Prashar, J.K. ibid., 839.
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23. 6. Lash, T.D. Org. Geochem. 1989, 14, 213. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A., Jr.; Bladel, K.A.; Feeley, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J., Jr.; Quizon, D.M.; Shiner, C.M.; Watson, A. Energy Fuels 1990, 4, 668. Lash, T.D.; Quizon-Colquitt, D.M.; Shiner, C.M.; Nguyen, T.H.; Hu, Z. Energy Fuels, 1993, 4, 668. Lash, T.D. In Advances in Nitrogen Heterocycles; Moody, C.J., Ed.; JAI Press, 1995, Vol. 1, 19-51.
24. 6. Lash, T.D. Org. Geochem. 1989, 14, 213. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A., Jr.; Bladel, K.A.; Feeley, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J., Jr.; Quizon, D.M.; Shiner, C.M.; Watson, A. Energy Fuels 1990, 4, 668. Lash, T.D.; Quizon-Colquitt, D.M.; Shiner, C.M.; Nguyen, T.H.; Hu, Z. Energy Fuels, 1993, 4, 668. Lash, T.D. In Advances in Nitrogen Heterocycles; Moody, C.J., Ed.; JAI Press, 1995, Vol. 1, 19-51.
25. 6. Lash, T.D. Org. Geochem. 1989, 14, 213. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A., Jr.; Bladel, K.A.; Feeley, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J., Jr.; Quizon, D.M.; Shiner, C.M.; Watson, A. Energy Fuels 1990, 4, 668. Lash, T.D.; Quizon-Colquitt, D.M.; Shiner, C.M.; Nguyen, T.H.; Hu, Z. Energy Fuels, 1993, 4, 668. Lash, T.D. In Advances in Nitrogen Heterocycles; Moody, C.J., Ed.; JAI Press, 1995, Vol. 1, 19-51.
26. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
27. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
28. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
29. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
30. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
31. 7. Lash, T.D.; Balasubramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809. May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909. Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273.
32. 8. a. Lash, T.D.; Johnson, M.C. Tetrahedron Lett. 1989, 30, 5697.
33. b. Lash, T.D.; Perun, T.J., Jr. ibid. 1987, 28, 6265.
34. 9. Lash, T.D.; Catarello, J.J. Tetrahedron 1993, 49, 4159. Quizon-Colquitt, D.M.; Lash, T.D. J. Heterocyclic Chem. 1993, 30, 477.
35. 9. Lash, T.D.; Catarello, J.J. Tetrahedron 1993, 49, 4159. Quizon-Colquitt, D.M.; Lash, T.D. J. Heterocyclic Chem. 1993, 30, 477.
36. 10. a. Lash, T.D. Tetrahedron Lett. 1988, 29, 6877;
37. b. Lash, T.D. Tetrahedron 1998, 54, 359.
38. 11. E.g.: Urbach, H.; Henning, R. Tetrahedron Lett. 1985, 26, 1839. Caspritz, G.; Alpermann, H.G.; Schleyerbach, R. Arzeim.-Forsch. 1986, 36, 1605.
39. 11. E.g.: Urbach, H.; Henning, R. Tetrahedron Lett. 1985, 26, 1839. Caspritz, G.; Alpermann, H.G.; Schleyerbach, R. Arzeim.-Forsch. 1986, 36, 1605.
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43. b. Smith, K.M.; Minnetian, O.M. J. Org. Chem. 1985, 50, 2073.
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45. 15. Lash, T.D.; Hoehner, M.C. J. Heterocyclic Chem. 1991, 28, 1671.
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47. 17. Surber, W.; Schinz, H. Helv. Chim. Acta 1954, 37, 1239.
48. 18. Prepared by adapting the procedure for ethyl 3-butylacetoacetate: Marvel, C.S.; Hager, F.D. Org. Synth. 1932, Coll. Vol. I, pp 248-250.
49. 19. Lash, T.D.; Bellettini, J.R.; Bastian, J.A.; Couch, K.B. Synthesis, 1994, 170. See also: Burns, D.H.; Jabara, C.S.; Burden, M.W. Synth. Comm. 1995, 25, 379. This strategy involves the condensation of nitroalkenes, or the related α-acetoxy-nitroalkanes with benzyl isocyanoacetate in the presence of a non-nucleophilic base and is based on ealier studies by others. See: Barton, D.H.R.; Kervagoret, J.; Zard, S.Z. Tetrahedron 1990, 46, 7587.
50. 19. Lash, T.D.; Bellettini, J.R.; Bastian, J.A.; Couch, K.B. Synthesis, 1994, 170. See also: Burns, D.H.; Jabara, C.S.; Burden, M.W. Synth. Comm. 1995, 25, 379. This strategy involves the condensation of nitroalkenes, or the related α-acetoxy-nitroalkanes with benzyl isocyanoacetate in the presence of a non-nucleophilic base and is based on ealier studies by others. See: Barton, D.H.R.; Kervagoret, J.; Zard, S.Z. Tetrahedron 1990, 46, 7587.
51. 19. Lash, T.D.; Bellettini, J.R.; Bastian, J.A.; Couch, K.B. Synthesis, 1994, 170. See also: Burns, D.H.; Jabara, C.S.; Burden, M.W. Synth. Comm. 1995, 25, 379. This strategy involves the condensation of nitroalkenes, or the related α-acetoxy-nitroalkanes with benzyl isocyanoacetate in the presence of a non-nucleophilic base and is based on ealier studies by others. See: Barton, D.H.R.; Kervagoret, J.; Zard, S.Z. Tetrahedron 1990, 46, 7587.
52. 20. Arsenault, G.P.; Bullock, E.; MacDonald, S.F. J. Am. Chem. Soc. 1960, 82, 4384. Cavaleiro, J.A.S.; Rocha Gonsalves, A.M. d'A.; Kenner, G.W.; Smith, K.M. J. Chem. Soc., Perkin Trans. I 1974, 1771.
53. 20. Arsenault, G.P.; Bullock, E.; MacDonald, S.F. J. Am. Chem. Soc. 1960, 82, 4384. Cavaleiro, J.A.S.; Rocha Gonsalves, A.M. d'A.; Kenner, G.W.; Smith, K.M. J. Chem. Soc., Perkin Trans. I 1974, 1771.
54. 21. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.
55. 21. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.
56. 21. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.