REAL

Facile syntheses of 3,4-disubstituted pyrroline nitroxides and their further synthetic applications

Úr, Györgyi and Kálai, Tamás and Hideg, Kálmán (2016) Facile syntheses of 3,4-disubstituted pyrroline nitroxides and their further synthetic applications. TETRAHEDRON LETTERS, 57 (7). pp. 778-780. ISSN 0040-4039

[img]
Preview
Text
TETL_47176(1).pdf

Download (1MB) | Preview

Abstract

Lithiation of an alfa,beta-unsaturated pyrroline nitroxide ester with LTMP at the beta-carbon followed by treatment with electrophiles led to a new series of 3,4-disubstituted pyrroline nitroxides, which could be used as valuable paramagnetic building blocks. The new compounds were tested in Sonogashira and Stille cross coupling reactions, which offered methyl 1-oxyl-4-substituted-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radicals for new C-C bond formation in poor to moderate yields. The reaction of an alfa,beta-unsaturated pyrroline nitroxide ester with methyl chloroformate generated diester 2b; the partial hydrolysis product of this reaction was shown to be a key compound for the synthesis of paramagnetic uracil derivative 10.

Item Type: Article
Uncontrolled Keywords: lithiation, Pd-catalyzed cross coupling, 2-nitrobenzyl protecting group, nitroxides, uracil
Subjects: Q Science / természettudomány > QD Chemistry / kémia
Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dr. Tamás Kálai
Date Deposited: 26 Jan 2016 12:48
Last Modified: 26 Jan 2016 12:48
URI: http://real.mtak.hu/id/eprint/32724

Actions (login required)

Edit Item Edit Item