Reactivity and regioselectivity of magnesium phenolates towards isatins: One-step synthesis of 3-(2-hydroxyaryl)-3-hydroxyindolones

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3981-3984

  Hewawasam, Piyasena ^a   Erway, Matthew ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; ISATIN DERIVATIVE; PHENOL DERIVATIVE;

ALKYLATION; ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032482493     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00741-2     Document Type: Article

References (13)

1. 1. Hewawasam, P.; Meanwell, N. A.; Gribkoff, V.; Dworetzky, S. I.; Boissard, C. G. Bioorg. Med. Chem. Lett. 1997, 7, 1255.
2. 2. (a) For a review on reactions of metal phenoxides with carbonyl compounds see: Casnati, G.; Casiraghi, G.; Pochini, A.; Sartori, G.; Ungaro, R. Pure & Appl. Chem. 1983, 55, 1677.
3. (b) Casiraghi, G.; Casnati, G.; Puglia, G.; Sartori, G.; Terenghi, G. J. Chem. Res. (S), 1977, 96; ibid. (M), 1977, 1123; Asgili, J. O.; Crombie, L.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1978, 59.
4. (b) Casiraghi, G.; Casnati, G.; Puglia, G.; Sartori, G.; Terenghi, G. J. Chem. Res. (S), 1977, 96; ibid. (M), 1977, 1123; Asgili, J. O.; Crombie, L.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1978, 59.
5. (b) Casiraghi, G.; Casnati, G.; Puglia, G.; Sartori, G.; Terenghi, G. J. Chem. Res. (S), 1977, 96; ibid. (M), 1977, 1123; Asgili, J. O.; Crombie, L.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1978, 59.
6. (c) Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A. Gazz. Chim. Ital. 1978, 108, 79.
7. (d) Bigi, F.; Casiraghi, G.; Casnati, G.; Marchesi, S.; Sartori, G. Tetrahedron 1984, 40, 4081;
8. Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. J. Chem. Soc., Perkin Trans. 1 1984, 2655.
9. (e) Casiraghi, G.; Casnati, G.; Cornia, M.; Sartori, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1974, 2077; Casnati, G.; Colli, M.; Pochini, A.; Ungaro, R. Chim. Ind. (Milan) 1977, 59, 764; Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, R.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1978, 318.
10. (e) Casiraghi, G.; Casnati, G.; Cornia, M.; Sartori, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1974, 2077; Casnati, G.; Colli, M.; Pochini, A.; Ungaro, R. Chim. Ind. (Milan) 1977, 59, 764; Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, R.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1978, 318.
11. (e) Casiraghi, G.; Casnati, G.; Cornia, M.; Sartori, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1974, 2077; Casnati, G.; Colli, M.; Pochini, A.; Ungaro, R. Chim. Ind. (Milan) 1977, 59, 764; Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, R.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1 1978, 318.
12. 3. Aryloxymagnesium bromides generated with ethyl magnesium bromide in ether solution were found to be quite insoluble in either methylene chloride or toluene. The success of the reaction was also dependent on the solubility of aryloxymagnesium bromides.
13. 3; C, 52.42; H, 2.64; N, 4.08. Found: C, 52.19; H, 2.57; N, 3.97.