Can I read 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 on EtoBox?

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 by Carlo Bonini; Lucia Chiummiento; Maria Funicello; Piero Spagnolo is a Chemistry article available to read on EtoBox.

What is 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 about?

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.

Who reads 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?

Author

Carlo Bonini; Lucia Chiummiento; Maria Funicello; Piero Spagnolo

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)