NDLI: A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions

Content Provider	Royal Society of Chemistry (RSC)
Author	Johnston, Jeffrey N. Tokumaru, Kazuyuki
Copyright Year	2017
Abstract	The 1,3,4-oxadiazole is an aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly, avoiding a 1,2-diacyl hydrazide intermediate. Access to new building blocks of oxadiazole-substituted secondary amines is improved by leveraging chiral α-bromo nitroalkane or amino acid hydrazide substrates. The non-dehydrative conditions for oxadiazole synthesis are particularly notable, in contrast to alternatives reliant on highly oxophilic reagents to effect cyclization of unsymmetrical 1,2-diacyl hydrazides. The mild conditions are punctuated by the straightforward removal of co-products by a standard aqueous wash.
Starting Page	3187
Ending Page	3191
Page Count	5
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	8
Issue Number	4
Journal	Chemical Science
DOI	10.1039/c7sc00195a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Nitro compound Bioisostere Carboxylic acid Hydrazide Chirality Carbonyl group Oxophilicity Heterocyclic compound Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Chemistry

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