Microwave-promoted Michael addition in neat water: A rapid, efficient and green method for the preparation of acyclic nucleosides

Synlett

Volumn , Issue 5, 2007, Pages 721-724

  Qu, Gui Rong ^a   Zhang, Zhi Guang ^a   Geng, Ming Wei ^a   Xia, Ran ^a   Zhao, Lin ^a   Guo, Hai Ming ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

Acyclic nucleoside; Green solvent; Michael addition; Microwave irradiation (MWI)

Indexed keywords

6 CHLOROPURINE; ACICLOVIR; ACRYLIC ACID; ACRYLONITRILE; ACYCLIC NUCLEOSIDE; CYTOSINE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE; WATER;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; MICROWAVE RADIATION; TECHNIQUE;

EID: 34047149817     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970772     Document Type: Article

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40. 2O (5 mL), acrylonitrile (6 mmol, 0.4 mL) was added. Then the mixture was put into the cavity of a commercially available single-mode microwave synthesis apparatus equipped with a high sensitivity infrared sensor for temperature control and measurement (MAS-I, Sineo Microwave Chemical Technology Co. Ltd., Shanghai, P. R. of China) and irradiated at 250 W (internal temperature: 100°C) for 5 min. After completion of the reaction, the mixture was concentrated to dryness under reduced pressure and the residue was purified by column chromatography using EtOAc-cyclohexane (9:1) as the eluent to afford 6a in 82% yield.
41. 6): δ = 1.094 (t, J = 6.8 Hz, 3 H), 3.014 (t, J = 6.8 Hz, 2 H), 4.013 (q, J = 7.2 Hz, 2 H), 4.532 (t, J = 6.8 Hz, 2 H), 8.689 (s, 1 H), 8.783 (s, 1 H) ppm.