Over several decades, many different strategies have been reported to prepare 4-, 5- , 6-, and 7- hydroxybenzofuran (HBF), which are very important synthetic intermediates. Interested in addition of their 2- lithiated O-protected derivatives to transient 1-pyrroline as a straightforward way to nicotinoids, we have developed a unique two-step procedure to obtain 4-, 5- , 6-, and 7-HBF from 2,6-, 2,5-, 2-4- and 2,3- dihydroxyacetophenone, respectively, by conversion into 4-, 5-, 6- and 7-hydroxybenzofuranone and successive reduction of these latter with lithium borohydride. On the basis of the overall yields, the number of steps and the availability of the starting materials, such a synthetic strategy can be advantageously compared with the literature methods, here briefly reviewed, developed to synthesize the four HBFs.(piture presented)

4-, 5-, 6-, and 7-Hydroxybenzofuran: a unified strategy for a two-step synthesis of versatile benzofuranic building blocks / R. Appiani, C. Morano, G. Roda, M. Pallavicini, C. Bolchi. - In: ARKIVOC. - ISSN 1551-7012. - 2022:5(2022 Jun), pp. 22-11791IP.259-22-11791IP.269. [10.24820/ark.5550190.p011.791]

4-, 5-, 6-, and 7-Hydroxybenzofuran: a unified strategy for a two-step synthesis of versatile benzofuranic building blocks

R. Appiani
Primo
;
C. Morano
Secondo
;
G. Roda;M. Pallavicini
Penultimo
;
C. Bolchi
Ultimo
2022-06-28

Abstract

Over several decades, many different strategies have been reported to prepare 4-, 5- , 6-, and 7- hydroxybenzofuran (HBF), which are very important synthetic intermediates. Interested in addition of their 2- lithiated O-protected derivatives to transient 1-pyrroline as a straightforward way to nicotinoids, we have developed a unique two-step procedure to obtain 4-, 5- , 6-, and 7-HBF from 2,6-, 2,5-, 2-4- and 2,3- dihydroxyacetophenone, respectively, by conversion into 4-, 5-, 6- and 7-hydroxybenzofuranone and successive reduction of these latter with lithium borohydride. On the basis of the overall yields, the number of steps and the availability of the starting materials, such a synthetic strategy can be advantageously compared with the literature methods, here briefly reviewed, developed to synthesize the four HBFs.(piture presented)
Hydroxybenzofuran; dihydroxyacetophenone; hydroxybenzofuranone; lithium borohydride;
Settore CHIM/06 - Chimica Organica
Settore CHIM/08 - Chimica Farmaceutica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/933126
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