An intramolecular cyclization of phenol derivatives bearing aminoquinones using a hypervalent iodine reagent

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 223-227

  Kita, Yasuyuki ^a   Takada, Takeshi ^a   Ibaraki, Megumi ^a   Gyoten, Michiyo ^a   Mihara, Sachiko ^a   Fujita, Shigekazu ^a   Tohma, Hirofumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001096403     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951439q     Document Type: Article

References (27)

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2. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
3. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
4. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
5. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
6. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
7. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
8. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
9. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
10. Reviews, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Varvoglis, A Chem. Soc Rev. 1981, 10, 377. (c) Koser, G. F. Hypervalent Halogen Compounds in The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18, p 721. (d) Varvoglis, A. Synthesis 1984, 709. (e) Moriarty, R. M.; Prakash, O. Acc Chem. Res. 1986, 19, 244. (f) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660. (g) Moriarty, R. M.; Valid, R. K.; Koser, G. F. Synlett 1990, 365. (h) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers, Inc.: New York, 1992. (i) Kita, Y.; Tohma, H.; Yakura, T. Trends Org. Chem. 1992, 3, 113. (j) Kita, Y.; Tohma, H. Farumasia 1992, 28, 984.
11. (a) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. Tetrahedron Lett. 1985, 26, 3837.
12. (b) Kita, Y.; Yakura, T.; Terashi, H.; Haruta, J.; Tamura, Y. Chem. Pharm. Bull. 1989, 37, 891 and references cited therein.
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15. (c) Tamura, Y.; Yakura, T.; Tohma, H.; Kikuchi, K.; Kita, Y. Synthesis 1989, 126.
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22. 2 under nitrogen and used without further purification; see ref 4a.
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24. An intramolecular nucleophilic substitution on an aryliodonium salt has been reported by us, see: Kita, Y.; Okunaka, R.; Kondo, M.; Tohma, H.; Inagaki, M.; Hatanaka, K. J. Chem Soc., Chem. Commun. 1992, 429.
25. 2NR, while they are nonreactive in the presence of weak nucleophiles; Spiroudis, A.; Varvoglis, A. J. Chem. Soc., Perkin Trans. 1 1984, 135.
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