Diels-Alder reactions of halogenated masked o-benzoquinones: synthesis of halogen-substituted bicyclo[2.2.2]octenones

Tetrahedron Letters

Volumn 50, Issue 7, 2009, Pages 773-775

  Surasani, Seshi Reddy ^a   Rajora, Virendra Singh ^a   Bodipati, Naganjaneyulu ^a   Peddinti, Rama Krishna ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZOQUINONE DERIVATIVE; 4 HALO 2 METHOXYPHENOL DERIVATIVE; ACRYLIC ACID METHYL ESTER; BICYCLO[2.2.2]OCTENONE DERIVATIVE; HALOGEN; IODINE; KETONE DERIVATIVE; METHACRYLIC ACID METHYL ESTER; METHYLVINYL KETONE; PHENOL DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; DIMERIZATION; ELECTRON; HALOGENATION; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

ALNUS;

EID: 58049180403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.117     Document Type: Article

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15. General procedure: Method A: To a solution of 4-halo-2-methoxyphenol (1 mM) and dienophile (25 mM) in anhydrous methanol (4 mL) was added a solution of DAIB (1.1 mM) in anhydrous methanol (6 mL) over a period of 30 min at 0 °C under nitrogen atmosphere. After 10 min, the ice bath was removed and the contents were allowed to stir at room temperature for the time specified in Table 1. After the reaction was complete, the reaction mixture was concentrated using a rotary evaporator under reduced pressure, and the residue was purified by silica gel column chromatography with 10% ethyl acetate in hexanes to furnish the cycloadduct.Method B: To a solution of 4-halo-2-methoxyphenol (1 mM) and dienophile (25 mM) in anhydrous methanol (4 mL) was added a solution of DAIB (1.1 mM) in anhydrous methanol (6 mL) over a period of 1 h at 50 °C under nitrogen atmosphere. The stirring was continued for 1 h at 50 °C for the reaction to reach completion, and then the products were purified as in method A.
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