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Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-8832

Landmesser, T; Linden, A; Hansen, H J (2008). A novel route to 1-substituted 3-(dialkylamino)-9-oxo-9H-indeno[2,1-c]pyridine-4-carbonitriles. Helvetica Chimica Acta, 91(2):265-284.

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Abstract

Heptalenecarbaldehydes 1/1’ as well as aromatic aldehydes react with 3-(dicyanomethylidene)-indan-1-one in boiling EtOH and in the presence of secondary amines to yield 3-(dialkylamino)-1,2-dihydro-9-oxo-9H-indeno[2,1-c]pyridine-4-carbonitriles (Schemes 2 and 4, and Fig. 1). The 1,2-dihydroforms can be dehydrogenated easily with KMnO4 in acetone at 08 (Scheme 3) or chloranil (¼2,3,5,6-
tetrachlorocyclohexa-2,5-diene-1,4-dione) in a 7one-pot8 reaction in dioxane at ambient temperature(Table 1). The structures of the indeno[2,1-c]pyridine-4-carbonitriles 5’ and 6a have been verified by Xraycrystal-structure analyses (Fig. 2 and 4). The inherent merocyanine system of the dihydro formsresults in a broad absorption band in the range of 515 – 530 nm in their UV/VIS spectra (Table 2 and
Fig. 3). The dehydrogenated compounds 5, 5’, and 7a – 7f exhibit their longest-wavelength absorptionmaximum at ca. 380 nm (Table 2). In contrast to 5 and 5’, 7a – 7f in solution exhibit a blue-greenfluorescence with emission bands at around 460 and 480 nm (Table 4 and Fig. 5).

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Institute of Organic Chemistry
DDC:540 Chemistry
Language:English
Date:2008
Deposited On:19 Jan 2009 13:59
Last Modified:27 Nov 2013 18:19
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Swiss National Science Foundation
Publisher DOI:10.1002/hlca.200890033
Official URL:http://dx.doi.org/10.1002/hlca.200890033
Other Identification Number:doi: 10.1002/hlca.200890033
Citations:Web of Science®. Times Cited: 2
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