KF/Al2O3/PEG-400: An Efficient Catalytic System for the Fiesselmann-Type Synthesis of Thiophene Derivatives

Pranjal Bezboruah; Pranjal Gogoi; Junali Gogoi; Romesh C. Boruah

doi:10.1055/s-0033-1338299

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1341-1348
DOI: 10.1055/s-0033-1338299

paper

KF/Al₂O₃/PEG-400: An Efficient Catalytic System for the Fiesselmann-Type Synthesis of Thiophene Derivatives

Pranjal Bezboruah

Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India Fax: +91(376)2370011 Email: gogoipranj@yahoo.co.uk Email: rc_boruah@yahoo.co.in

,

Pranjal Gogoi*

Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India Fax: +91(376)2370011 Email: gogoipranj@yahoo.co.uk Email: rc_boruah@yahoo.co.in

,

Junali Gogoi

Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India Fax: +91(376)2370011 Email: gogoipranj@yahoo.co.uk Email: rc_boruah@yahoo.co.in

,

Romesh C. Boruah*

Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India Fax: +91(376)2370011 Email: gogoipranj@yahoo.co.uk Email: rc_boruah@yahoo.co.in

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Abstract

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Abstract

A simple and mild protocol has been developed for the synthesis of novel steroidal and nonsteroidal thiophene derivatives from β-halo-α,β-unsaturated aldehydes using KF/Al₂O₃/PEG-400 as an efficient catalytic system. The β-halo-α,β-unsaturated aldehydes are synthesized from the corresponding ketones using Vilsmeier formylation reaction and converted into β-halo-α,β-unsaturated nitriles. The synthetic protocol is subsequently applied to the synthesis of 3-aminothiophene derivatives using β-halo-α,β-unsaturated nitriles.

Key words

Fiesselmann synthesis - KF/Al₂O₃/PEG-400 - thiophene - unsaturated aldehyde - unsaturated nitrile

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References

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