Triazole photonucleases: A new family of light activatable DNA cleaving agents

Journal of the American Chemical Society

Volumn 118, Issue 27, 1996, Pages 6522-6523

  Wender, Paul A ^a   Touami, Sofia M ^a   Alayrac, Carole ^a   Philipp, Ulrich C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLE DERIVATIVE;

ARTICLE; DNA CLEAVAGE; PHOTOCHEMISTRY;

EID: 0029945735     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960647c     Document Type: Article

References (40)

1. For recent reviews, see: Enedivne Antibiotics As Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. Tetrahedron Symposia-In-Print Number 53; Doyle, T. W., Kadow, J. F., Eds.; Elsevier: Oxford, 1994; Vol. 50, pp 1311-1538.
2. For recent reviews, see: Enedivne Antibiotics As Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. Tetrahedron Symposia-In-Print Number 53; Doyle, T. W., Kadow, J. F., Eds.; Elsevier: Oxford, 1994; Vol. 50, pp 1311-1538.
3. For recent reviews, see: Enedivne Antibiotics As Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. Tetrahedron Symposia-In-Print Number 53; Doyle, T. W., Kadow, J. F., Eds.; Elsevier: Oxford, 1994; Vol. 50, pp 1311-1538.
4. For recent reviews, see: Enedivne Antibiotics As Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. Tetrahedron Symposia-In-Print Number 53; Doyle, T. W., Kadow, J. F., Eds.; Elsevier: Oxford, 1994; Vol. 50, pp 1311-1538.
5. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
6. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
7. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
8. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
9. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
10. For lead references on other nucleic acid cleaving agents, see: Singh, U. S.; Scanned, R. T.; An, H.; Carter, B. J.; Hecht, S. M. J. Am. Chem. Soc. 1995, 117, 12691-12699. Chen, C.-H.; Garin, M. B.; Sigman, D. S. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 4206-4210. Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086. Dervan, P. B. In Structure & Methods; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Schenectady, NY, 1990; Vol. 1, pp 37-50. Shields, T. P.; Barton, J. K. Biochemistry 1995, 34, 15037-15048. Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769 and references cited therein.
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14. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
15. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
16. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
17. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
18. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
19. Significant contributions have been made by several groups, including those of Bruckner, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. For lead references and examples, see: ref 1. Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 62, 16-44. Myers, A. G.; Fraley, M. E.; Tom, N. J.; Cohen, S. B.; Madar, D. J. Chem. Biol. 1995, 2, 33-43. Smith, A. L.; Pitsinos, E. N.; Hwang, C.-K.; Mizuno, Y.; Saimolo, H.; Scarlato, G. R.; Suzuki, T.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7612-7624. Magnus, P. Tetrahedron 1994, 50, 1397-1418. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419-1434.
20. Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am Chem. Soc. 1977, 99, 7589-7600. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614. Bridger, R. T.; Russell, G. A. J. Am Chem. Soc. 1963, 85, 3754-3766. Madhavan, V.; Schuler, R. H.; Fessenden, R. W. J. Am. Chem. Soc. 1978, 100, 888-893.
21. Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am Chem. Soc. 1977, 99, 7589-7600. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614. Bridger, R. T.; Russell, G. A. J. Am Chem. Soc. 1963, 85, 3754-3766. Madhavan, V.; Schuler, R. H.; Fessenden, R. W. J. Am. Chem. Soc. 1978, 100, 888-893.
22. Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am Chem. Soc. 1977, 99, 7589-7600. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614. Bridger, R. T.; Russell, G. A. J. Am Chem. Soc. 1963, 85, 3754-3766. Madhavan, V.; Schuler, R. H.; Fessenden, R. W. J. Am. Chem. Soc. 1978, 100, 888-893.
23. Kryger, R. G.; Lorand, J. P.; Stevens, N. R.; Herron, N. R. J. Am Chem. Soc. 1977, 99, 7589-7600. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614. Bridger, R. T.; Russell, G. A. J. Am Chem. Soc. 1963, 85, 3754-3766. Madhavan, V.; Schuler, R. H.; Fessenden, R. W. J. Am. Chem. Soc. 1978, 100, 888-893.
24. Notable exceptions include studies on the use of trimethylene methane diradicals from diazo extrusions and phenyl radicals from diazene and diazonium ion decompositions: Bregant, T. M.; Groppe, J.; Little, R. D. J. Am. Chem. Soc. 1994, 116, 3635-3636. Jebaratman, D. J: Kugabalasooriar, S.; Cher, H.; Arya, D. P. Tetrahedron Lett. 1995, 36, 3123-3126. Griffiths, J.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1992, 24-26. See also: Sullivan, R. W.; Coghlan, V. M.; Munk, S. A.; Reed, M. W.; Moore, H. W. J. Org. Chem. 1994, 59, 2276-2278.
25. Notable exceptions include studies on the use of trimethylene methane diradicals from diazo extrusions and phenyl radicals from diazene and diazonium ion decompositions: Bregant, T. M.; Groppe, J.; Little, R. D. J. Am. Chem. Soc. 1994, 116, 3635-3636. Jebaratman, D. J: Kugabalasooriar, S.; Cher, H.; Arya, D. P. Tetrahedron Lett. 1995, 36, 3123-3126. Griffiths, J.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1992, 24-26. See also: Sullivan, R. W.; Coghlan, V. M.; Munk, S. A.; Reed, M. W.; Moore, H. W. J. Org. Chem. 1994, 59, 2276-2278.
26. Notable exceptions include studies on the use of trimethylene methane diradicals from diazo extrusions and phenyl radicals from diazene and diazonium ion decompositions: Bregant, T. M.; Groppe, J.; Little, R. D. J. Am. Chem. Soc. 1994, 116, 3635-3636. Jebaratman, D. J: Kugabalasooriar, S.; Cher, H.; Arya, D. P. Tetrahedron Lett. 1995, 36, 3123-3126. Griffiths, J.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1992, 24-26. See also: Sullivan, R. W.; Coghlan, V. M.; Munk, S. A.; Reed, M. W.; Moore, H. W. J. Org. Chem. 1994, 59, 2276-2278.
27. Notable exceptions include studies on the use of trimethylene methane diradicals from diazo extrusions and phenyl radicals from diazene and diazonium ion decompositions: Bregant, T. M.; Groppe, J.; Little, R. D. J. Am. Chem. Soc. 1994, 116, 3635-3636. Jebaratman, D. J: Kugabalasooriar, S.; Cher, H.; Arya, D. P. Tetrahedron Lett. 1995, 36, 3123-3126. Griffiths, J.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1992, 24-26. See also: Sullivan, R. W.; Coghlan, V. M.; Munk, S. A.; Reed, M. W.; Moore, H. W. J. Org. Chem. 1994, 59, 2276-2278.
28. Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278-1282.
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30. For lead references, see: Shizuka, H.; Hiratsuka, H.; Jinguji, M.; Hiraoka, H. J. Phys. Chem. 1987, 91, 1793-1797. Murai, H.; Torres, M.; Strausz, O. P. J. Am. Chem. Soc. 1980, 102, 1421-1422. Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.; Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.; Murky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli, A.; Hansen, H. J.; Schmid, H. Pure Appl. Chem. 1973, 33, 339-361. Burgess, E. M.; Carithers, R.; McCullagh, L. J. Am. Chem. Soc. 1968, 90, 1923-1924. Boyer, H.; Selvarajan, R. J. Heterocycl. Chem. 1969, 6, 503-506. Tsujimoto, K.; Ohashi, M.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1972, 45, 515-519.
31. For lead references, see: Shizuka, H.; Hiratsuka, H.; Jinguji, M.; Hiraoka, H. J. Phys. Chem. 1987, 91, 1793-1797. Murai, H.; Torres, M.; Strausz, O. P. J. Am. Chem. Soc. 1980, 102, 1421-1422. Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.; Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.; Murky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli, A.; Hansen, H. J.; Schmid, H. Pure Appl. Chem. 1973, 33, 339-361. Burgess, E. M.; Carithers, R.; McCullagh, L. J. Am. Chem. Soc. 1968, 90, 1923-1924. Boyer, H.; Selvarajan, R. J. Heterocycl. Chem. 1969, 6, 503-506. Tsujimoto, K.; Ohashi, M.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1972, 45, 515-519.
32. For lead references, see: Shizuka, H.; Hiratsuka, H.; Jinguji, M.; Hiraoka, H. J. Phys. Chem. 1987, 91, 1793-1797. Murai, H.; Torres, M.; Strausz, O. P. J. Am. Chem. Soc. 1980, 102, 1421-1422. Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.; Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.; Murky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli, A.; Hansen, H. J.; Schmid, H. Pure Appl. Chem. 1973, 33, 339-361. Burgess, E. M.; Carithers, R.; McCullagh, L. J. Am. Chem. Soc. 1968, 90, 1923-1924. Boyer, H.; Selvarajan, R. J. Heterocycl. Chem. 1969, 6, 503-506. Tsujimoto, K.; Ohashi, M.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1972, 45, 515-519.
33. For lead references, see: Shizuka, H.; Hiratsuka, H.; Jinguji, M.; Hiraoka, H. J. Phys. Chem. 1987, 91, 1793-1797. Murai, H.; Torres, M.; Strausz, O. P. J. Am. Chem. Soc. 1980, 102, 1421-1422. Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.; Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.; Murky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli, A.; Hansen, H. J.; Schmid, H. Pure Appl. Chem. 1973, 33, 339-361. Burgess, E. M.; Carithers, R.; McCullagh, L. J. Am. Chem. Soc. 1968, 90, 1923-1924. Boyer, H.; Selvarajan, R. J. Heterocycl. Chem. 1969, 6, 503-506. Tsujimoto, K.; Ohashi, M.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1972, 45, 515-519.
34. For lead references, see: Shizuka, H.; Hiratsuka, H.; Jinguji, M.; Hiraoka, H. J. Phys. Chem. 1987, 91, 1793-1797. Murai, H.; Torres, M.; Strausz, O. P. J. Am. Chem. Soc. 1980, 102, 1421-1422. Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.; Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.; Murky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli, A.; Hansen, H. J.; Schmid, H. Pure Appl. Chem. 1973, 33, 339-361. Burgess, E. M.; Carithers, R.; McCullagh, L. J. Am. Chem. Soc. 1968, 90, 1923-1924. Boyer, H.; Selvarajan, R. J. Heterocycl. Chem. 1969, 6, 503-506. Tsujimoto, K.; Ohashi, M.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1972, 45, 515-519.
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