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. 2010 Apr 30;15(5):3211-27.
doi: 10.3390/molecules15053211.

Bohlmann-Rahtz cyclodehydration of aminodienones to pyridines using N-iodosuccinimide

Mark C Bagley  1 , Christian Glover
Affiliations

Bohlmann-Rahtz cyclodehydration of aminodienones to pyridines using N-iodosuccinimide

Mark C Bagley et al. Molecules. .

Abstract

Cyclodehydration of Bohlmann-Rahtz aminodienone intermediates using N-iodosuccinimide as a Lewis acid proceeds at low temperature under very mild conditions to give the corresponding 2,3,6-trisubstituted pyridines in high yield and with total regiocontrol.

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Figures

Scheme 1
Scheme 1
Two-step Bohlmann-Rahtz synthesis of 2,3,6-trisubstituted pyridines 4.
Scheme 2
Scheme 2
Synthesis of 3-iodo-2(1H)-pyridinone 6 from δ-dienaminoester 5 by Dechoux and co-workers [36].
Scheme 3
Scheme 3
Possible mechanistic course (path a, b or c) of the reaction between Bohlmann-Rahtzaminodienones 3 and NIS.
Scheme 4
Scheme 4
Enamine and aryl ethynylketone subsets, 1a-c and 2b-d, respectively.
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References

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    1. Bagley M.C., Glover C., Merritt E.A. The Bohlmann–Rahtz pyridine synthesis: from discovery to applications. Synlett. 2007:2459–2482.

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