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Volumn 51, Issue 2, 2010, Pages 363-366

Palladium-catalyzed double allylic alkylation of indole-2-hydroxamates: easy access to pyrazino[1,2-a]indole derivatives

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PALLADIUM; PYRAZINE DERIVATIVE; PYRAZINO(1,2 A)INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 71049154982 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/j.tetlet.2009.11.031 Document Type: Article

Times cited : (16)

References (10)

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- Bös, M.¹ Jenck, F.² Moreau, J.L.³ Mutel, V.⁴ Sleight, A.J.⁵ Widmer, U.⁶

2
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9
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- note
- 3 (0.3 equiv) in DCM or DCE. The reaction was stirred at room temperature until completion as determined by HPLC. The crude reaction mixture was then concentrated and purified by silica gel chromatography.

10
- 23644438030
- The indole-2-hydroxamates were prepared according to a modified version of To a stirred mixture of ethyl-5-chloroindole-2-carboxylate (1.0 equiv) and O-t-butylhydroxylamine hydrochloride (1.2 equiv) in THF (0.2 M) at -78 °C was added dropwise LiHMDS 1 M THF solution (5 equiv). The solution was stirred at -20 °C for 1 h. Work-up followed by trituration in 10% ether/hexanes afforded the product in 95% yield. In some cases the hydroxamates were synthesised using indole-2-carboxylic acid and hydroxlamines via standard peptidic coupling
- The indole-2-hydroxamates were prepared according to a modified version of. Gissot A., Volonterio A., and Zanda M. J. Org. Chem. 70 (2005) 6925 To a stirred mixture of ethyl-5-chloroindole-2-carboxylate (1.0 equiv) and O-t-butylhydroxylamine hydrochloride (1.2 equiv) in THF (0.2 M) at -78 °C was added dropwise LiHMDS 1 M THF solution (5 equiv). The solution was stirred at -20 °C for 1 h. Work-up followed by trituration in 10% ether/hexanes afforded the product in 95% yield. In some cases the hydroxamates were synthesised using indole-2-carboxylic acid and hydroxlamines via standard peptidic coupling
- (2005) J. Org. Chem. , vol.70 , pp. 6925
- Gissot, A.¹ Volonterio, A.² Zanda, M.³

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