Partial reduction of annulated heterocycles as a general route to medium rings containing oxygen and nitrogen

Organic Letters

Volumn 3, Issue 6, 2001, Pages 861-864

  Donohoe, Timothy J ^a   Raoof, Ali ^a   Linney, Ian D ^a   Helliwell, Madeleine ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HETEROCYCLIC COMPOUND; NITROGEN; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS;

HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROGEN; OXYGEN;

EID: 0035932581     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007035o     Document Type: Article

References (29)

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20. CCDC deposition number for 14 is 156092.
21. Representative experimental procedure: Lithium (27 mg, 3.8 mmol) was added to freshly distilled ammonia (50 mL) and allowed to stir at -78°C under an atmosphere of nitrogen for 2 h before the addition of bis-(2-methoxyethyl)amine (5 mL, 30 mmol). Compound 11 (200 mg, 0.96 mmol) was dissolved in THF (25 mL) and added to the reaction mixture after 5 min. The resultant solution was allowed to stir at -78°C for 2.5 h before the addition of isoprene (50 μL), immediately followed by methyl iodide (2 mL, 32 mmol). After an additional 1 h, the resultant bright yellow solution was treated with a saturated ammonium chloride solution (5 mL) before being allowed to warm to room temperature over 16 h. The reaction mixture was extracted into diethyl ether (3 x 50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford a yellow oil. Purification by chromatography (silica, petroleum ether-diethyl ether, 9:1 v/v) afforded compound 17 (140 mg, 65%) as a colorless oil.
22. 2 for 10 min before the addition of dimethyl sulfide (0.16 mL, 2.2 mmol). The reaction mixture was allowed to warm to room temperature over 16 h. The resultant solution was washed with brine (2 x 5 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford compound 19 (59 mg, 100%) as a pale yellow oil which did not require further purification.
23. Care must be taken with these compounds as an intramolecular aldol reaction takes place on exposure to silica.
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