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Fused-Ring Nitrogen and Sulfur Heterocycles by a Tandem SN2-Michael Addition Reaction.

✍ Scribed by Richard A. Bunce; Sharadsrikar V. Kotturi; Christopher J. Peeples; Elizabeth M. Holt


Publisher
John Wiley and Sons
Year
2003
Weight
153 KB
Volume
34
Category
Article
ISSN
0931-7597

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## Abstract A tandem S~N~2‐Michael addition reaction has been developed for the synthesis of __cis__‐ and __trans__‐fused nitrogen and sulfur heterocycles from the __cis__ and __trans__ isomers of ethyl (±)‐(2__E__)‐3‐[2‐(iodomethyl)cyclo‐hexyl]‐2‐propenoate. Octahydro‐1__H__‐isoindole‐1‐acetic aci

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## Abstract magnified image Benzo‐fused heterocyclic and carbocyclic systems have been synthesized by intramolecular S~N~Ar and tandem S~N~2‐S~N~Ar reactions. Treatment of 3‐(2‐fluoro‐5‐nitrophenyl)‐1‐propanol with sodium hydride in __N,N__‐dimethylformamide gave 6‐nitrochroman in 80% yield by an

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