On the syntheses of thiophene analogs of practolol and “reversed” practolol

…, S Conde, C Corral, J Lissavetzky

Index: Casarrubio; Conde; Corral; Lissavetzky Journal of Heterocyclic Chemistry, 1983 , vol. 20, # 6 p. 1557 - 1560

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Citation Number: 3

Abstract

Abstract The synthesis of the thiophene analogs of the cardio-selective β-adrenergic blocking agents Practolol and “reversed” Practolol has been attempted starting from 2-acetyl- 5-bromothiophene. Although this synthesis worked for the second compound it was not possible to obtain the first one. From this and other results of this paper it can be deduced that the thiophene analog of Practolol must be an unstable compound.

 Related Synthetic Route
1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~75%

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

Solketal Structure

100-79-8

Solketal

~%

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

1-(5-methylcarbamoyl-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-79-8

1-(5-methylcarb...

~83%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

~%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

(Z)-1-(5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)thiophen-2-yl)ethan-1-one oxime Structure

89724-78-7

(Z)-1-(5-((2,2-...

~%

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

Ethylene glycol Structure

107-21-1

Ethylene glycol

~94%

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

(Z)-1-(5-(oxiran-2-ylmethoxy)thiophen-2-yl)ethan-1-one oxime Structure

89724-85-6

(Z)-1-(5-(oxira...

~72%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-[5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]thiophen-2-yl]ethanone Structure

89724-76-5

1-[5-[(2,2-dime...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

(Z)-1-(5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)thiophen-2-yl)ethan-1-one oxime Structure

89724-78-7

(Z)-1-(5-((2,2-...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

5-(2,3-dihydroxypropoxy)-N-methylthiophene-2-carboxamide Structure

89724-80-1

5-(2,3-dihydrox...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-(5-methylcarbamoyl-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-79-8

1-(5-methylcarb...

~%

N-methyl-5-(oxiran-2-ylmethoxy)thiophene-2-carboxamide Structure

89724-81-2

N-methyl-5-(oxi...

1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~92%

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

~%

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~%

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethanone Structure

89724-83-4

1-[5-(oxiran-2-...

~36%

(Z)-1-(5-(oxiran-2-ylmethoxy)thiophen-2-yl)ethan-1-one oxime Structure

89724-85-6

(Z)-1-(5-(oxira...

N-[1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethylidene]hydroxylamine Structure

89724-84-5

N-[1-[5-(oxiran...

2-Acetyl-5-bromothiophene Structure

5370-25-2

2-Acetyl-5-brom...

~%

N-[1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethylidene]hydroxylamine Structure

89724-84-5

N-[1-[5-(oxiran...

2-(5-bromothiophen-2-yl)-2-methyl-1,3-dioxolane Structure

6909-65-5

2-(5-bromothiop...

~%

N-[1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethylidene]hydroxylamine Structure

89724-84-5

N-[1-[5-(oxiran...

1-[5-(2,3-dihydroxypropoxy)thiophen-2-yl]ethanone Structure

89724-82-3

1-[5-(2,3-dihyd...

~%

N-[1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethylidene]hydroxylamine Structure

89724-84-5

N-[1-[5-(oxiran...

1-(5-(2-methyl-1,3-dioxolan-2-yl)-2-thienyloxy)-2,3-O-isopropylidenepropane Structure

89724-75-4

1-(5-(2-methyl-...

~%

N-[1-[5-(oxiran-2-ylmethoxy)thiophen-2-yl]ethylidene]hydroxylamine Structure

89724-84-5

N-[1-[5-(oxiran...


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