New reactions of hydrazides. Part 1: Directed ortho- and lateral metalation of aromatic carbocyclic and heterocyclic systems

Authors
McCombie, SW Lin, SI Vice, SF
Citation
Sw. Mccombie et al., New reactions of hydrazides. Part 1: Directed ortho- and lateral metalation of aromatic carbocyclic and heterocyclic systems, TETRAHEDR L, 40(50), 1999, pp. 8767-8770
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
50
Year of publication
1999
Pages
8767 - 8770
Database
ISI
SICI code
0040-4039(199912)40:50<8767:NROHP1>2.0.ZU;2-B
Abstract
Aromatic and heterocyclic 2,2-dialkylhydrazides undergo directed metalation with 2 equivalents of n-, s- or t-BuLi, and the resulting C,N-dilithio spe cies react with a variety of electrophiles. The products may be readily con verted to the corresponding carboxylic acids or esters by oxidation with ma nganese dioxide in water or methanol containing acetic acid. (C) 1999 Publi shed by Elsevier Science Ltd. All rights reserved.