Alkynylbenzotriazoles by direct alkynylation of benzotriazole using alkynyliodonium salts

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3787-3790

  Kitamura, Tsugio ^a   Tashi, Norihiko ^a   Tsuda, Kuniyuki ^a   Fujiwara, Yuzo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLPHENYLIODONIUM TOSYLATE; BENZOTRIAZOLE DERIVATIVE; POTASSIUM BUTOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; DNA CLEAVAGE; ORGANIC CHEMISTRY; PHYTOCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032575146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00617-0     Document Type: Article

References (28)

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7. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
8. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
9. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
10. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
11. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
12. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
13. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
14. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
15. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
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17. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
18. 5. For recent reviews and books, see: Koser, G. F. in The Chemistry of Functional Groups, Supplement D; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: New York, 1983; Chapters 18 and 25; Varvoglis, A. Synthesis 1984, 709-726; Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244-250; Merkushev, E. B. Russ. Chem. Rev. (Eng. Transl.) 1987, 56, 826-845; Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431-447; Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365-383; Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992; Kita, Y.; Tohma, H.; Yakura, T. Trends in Organic Chemistry 1992, 3, 113-128; Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221-227; Kitamura, T. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 893-905; Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123-1178; Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997; Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409-458.
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21. 6. Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokai Shi 1986, 44, 660-673; Ochiai, M. Rev. Heteroatom Chem. 1989, 2, 92-111; Stang, P. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 274-285; Stang, P. J. in Supplement C: The chemistry of triple-bonded functional groups; Patai, S. Ed.; John Wiley & Sons: Chichester, 1994, Chapter 20; Stang, P. J. ref. 3, Chapter 3.
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28. 2), 6.79 (s, =CH), 7.3-7.5 (m, ArH).