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N-(3-Benzo[b]thienyl)iminophosphoranes toward the Synthesis of Benzo[b]thieno[3,2-b]pyridines: Reactivity and Alternative Regioselectivity with α,β-unsaturated Ketones and Aldehydes

✍ Scribed by Carlo Bonini; Lucia Chiummiento; Maria Funicello; Piero Spagnolo

Book ID
104202514
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
92 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

The novel N- (3-benzo[b]thienyl)iminophosphoranes 1b-d react with a,b-unsaturated aldehydes and ketones 2a-e to give varying mixtures of the regioisomeric benzothieno[3,2-b]pyridines 3a-d and 4a-d as a result of preferential attack of either imino nitrogen or a-thienyl carbon at the enone carbonyl group. The findings indicate that the progressive replacement of phenyl with methyl P-substituent greatly enhances the reactivity of the phosphorane 1 and concomitantly enhances the propensity of the phosphorane itself for addition to the enone by the a-thienyl carbon.

📜 SIMILAR VOLUMES

ChemInform Abstract: Novel N-(2-Benzo[b]
ChemInform Abstract: Novel N-(2-Benzo[b]thienyl)iminophosphoranes and Their Use in the Synthesis of Benzo[b]thieno[2,3-b]pyridines.
✍ Carlo Bonini; Maurizio D'Auria; Maria Funicello; Gianfranco Romaniello 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views

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