79917-39-8Relevant academic research and scientific papers
Catalytic Enantioselective Nitroso Diels-Alder Reaction
Maji, Biplab,Yamamoto, Hisashi
supporting information, p. 15957 - 15963 (2016/01/09)
The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synthesis of 3,6-dihydro-1,2-oxazines and 1-amino-4-hydroxy-2-ene derivatives. Herein we report the Cu(I)-DTBM-Segphos catalyzed asymmetric intermolecular NDA reaction of variously substituted cyclic 1,3-dienes using highly reactive nitroso compounds derived from pyrimidine and pyridazine derivatives. In most of the cases studied, the cycloadducts were obtained in high yields (up to 99%) with very high regio-, diastereo-, and enantioselectivities (up to regioselectivity > 99:1, d.r. > 99:1, and >99% ee). As an application of this methodology, formal syntheses of conduramine A-1 and narciclasine were accomplished.
Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions
Yang, Baiyuan,Zoellner, Tina,Gebhardt, Peter,Moellmann, Ute,Miller, Marvin J.
experimental part, p. 691 - 697 (2010/05/12)
A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels-Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N-O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.
CATALTYTIC ASYMMETRIC HETERO DIELS-ALDER REACTION OF A HETEROAROMATIC C-NITROSO DIENOPHILE: A NOVEL METHOD FOR SYNTHESIS OF CHIRAL NON-RACEMIC AMINO ALCOHOLS
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Page/Page column 42, (2010/02/13)
The present invention is directed to a catalytic asymmetric C-nitroso Diels-Alder reaction.
SYNTHESIS AND PROPERTIES OF PHENYL(METHYL)-SUBSTITUTED 2- AND 4-NITROSOPYRIMIDINES
Moskalenko, G. G.,Sedova, V. F.,Mamaev, V. P.
, p. 805 - 811 (2007/10/02)
Phenyl(methyl)-substituted 2- and 4-nitroso- and azoxypyrimidines were synthesized for the first time by the oxidation of phenyl(methyl)-substituted 2- and 4-hydroxyaminopyrimidines by activated MnO2, Ag2CO3 on zeolite, or BaMnO4.Certain chemical properti
Conversion of a Primary Amino Group into a Nitroso Group. Synthesis of Nitroso-Substituted Heterocycles
Taylor, Edward C.,Tseng, Chi-Ping,Rampal, Jang B.
, p. 552 - 555 (2007/10/02)
2-Aminopyridine, 2-amino-4-methylpyridine, 1-aminoisoquinoline, 2-aminopyrimidine, and 2-aminopyrazine have been converted to the corresponding nitroso compounds by reaction with dimethyl sulfide and N-chlorosuccinimide, deprotonation of the resulting sul
