Sequential reduction and dehydration of phenacyl-(E)-styryl sulfones to unsymmetrical (E,E)-bis(styryl) sulfones

Muralidhar Reddy Mallireddigari; Venkat R. Pallela; E. Premkumar Reddy; M. V.Ramana Reddy

doi:10.1055/s-2005-918450

Sequential reduction and dehydration of phenacyl-(E)-styryl sulfones to unsymmetrical (E,E)-bis(styryl) sulfones

Muralidhar Reddy Mallireddigari, Venkat R. Pallela, E. Premkumar Reddy, M. V.Ramana Reddy

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH₄ reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF₃·Et₂O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH₄ in EtOH followed by refluxing with concentrated HCl.

Original language	English
Article number	M00605SS
Pages (from-to)	3639-3643
Number of pages	5
Journal	Synthesis
Issue number	20
DOIs	https://doi.org/10.1055/s-2005-918450
State	Published - 20 Dec 2005
Externally published	Yes

Keywords

(E,E)-bis(styryl) sulfones
Knoevenagel condensation
Styrylsulfinate
β-Hydroxy-(E)-vinylic sulfones
β-Keto vinylic sulfones

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10.1055/s-2005-918450

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title = "Sequential reduction and dehydration of phenacyl-(E)-styryl sulfones to unsymmetrical (E,E)-bis(styryl) sulfones",

abstract = "β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH4 reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF3·Et2O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH4 in EtOH followed by refluxing with concentrated HCl.",

keywords = "(E,E)-bis(styryl) sulfones, Knoevenagel condensation, Styrylsulfinate, β-Hydroxy-(E)-vinylic sulfones, β-Keto vinylic sulfones",

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year = "2005",

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doi = "10.1055/s-2005-918450",

language = "English",

pages = "3639--3643",

journal = "Synthesis",

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TY - JOUR

T1 - Sequential reduction and dehydration of phenacyl-(E)-styryl sulfones to unsymmetrical (E,E)-bis(styryl) sulfones

AU - Mallireddigari, Muralidhar Reddy

AU - Pallela, Venkat R.

AU - Reddy, E. Premkumar

AU - Reddy, M. V.Ramana

PY - 2005/12/20

Y1 - 2005/12/20

N2 - β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH4 reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF3·Et2O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH4 in EtOH followed by refluxing with concentrated HCl.

AB - β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH4 reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF3·Et2O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH4 in EtOH followed by refluxing with concentrated HCl.

KW - (E,E)-bis(styryl) sulfones

KW - Knoevenagel condensation

KW - Styrylsulfinate

KW - β-Hydroxy-(E)-vinylic sulfones

KW - β-Keto vinylic sulfones

UR - http://www.scopus.com/inward/record.url?scp=29744439505&partnerID=8YFLogxK

U2 - 10.1055/s-2005-918450

DO - 10.1055/s-2005-918450

M3 - Article

AN - SCOPUS:29744439505

SN - 0039-7881

SP - 3639

EP - 3643

JO - Synthesis

JF - Synthesis

IS - 20

M1 - M00605SS

ER -

Sequential reduction and dehydration of phenacyl-(E)-styryl sulfones to unsymmetrical (E,E)-bis(styryl) sulfones

Abstract

Keywords

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