THE FISCHER INDOLIZATION REACTION AND THE SYNTHESIS OF DIHYDROINDENOINDOLES

Authors
BROWN DW MAHON MF NINAN A SAINSBURY M SHERTZER HG
Citation
Dw. Brown et al., THE FISCHER INDOLIZATION REACTION AND THE SYNTHESIS OF DIHYDROINDENOINDOLES, Tetrahedron, 49(39), 1993, pp. 8919-8932
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
39
Year of publication
1993
Pages
8919 - 8932
Database
ISI
SICI code
0040-4020(1993)49:39<8919:TFIRAT>2.0.ZU;2-#
Abstract
The Fischer reaction between indanones and certain alkoxyarylhydrazine s fails; the indanones are returned unreacted and the arylhydrazines a re converted into the corresponding alkoxy-2-chloroarylamines and othe r products. A new N-amination route to arylhydrazines from the arylami nes has been developed and it has been demonstrated that problems with the indolisation of alkoxyarylhydrazones can be circumvented by ring closures of their O-tosylated analogues. Some results using the Lepke synthesis of indoles are recorded.