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Study of the pyrimidine nucleobase C5C6 bond reactivity under thio-michael/aldol tandem reaction conditions

✍ Scribed by Edna Vázquez Velez; Céline Desnous; Pascale Clivio

Publisher: Journal of Heterocyclic Chemistry
Year: 2006
Tongue: English
Weight: 86 KB
Volume: 43
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570430442

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✦ Synopsis

Abstract

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Pyrimidine nucleobases can undergo a Michael/aldol tandem reaction triggered by a thiolate. In an intramolecular context, 5′‐deoxy‐2′,3′‐isopropylidene‐5′‐thiouridine affords the reminiscent Baylis‐Hillman adduct after retro‐Michael addition whereas its thymine counterpart is unreactive. In an intermolecular context, the conjugate addition‐aldol reaction occurs only if the C5C6 double bond is activated.

📜 SIMILAR VOLUMES

Study of the Pyrimidine Nucleobase C5—C6

Study of the Pyrimidine Nucleobase C5—C6 Bond Reactivity under Thio-Michael/Aldol Tandem Reaction Conditions.

✍ Edna Vazquez Velez; Celine Desnous; Pascale Clivio 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 20 KB

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