76460-87-2Relevant academic research and scientific papers
Nickel-catalyzed sp3 C-H bond activation from decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with amides
Zhang, Jia-Xiang,Wang, Yan-Jing,Wang, Nai-Xing,Zhang, Wei,Bai, Cui-Bing,Li, Yi-He,Wen, Jia-Long
, p. 1621 - 1625 (2014/07/08)
Nickel-catalyzed functionalization of C(sp3)-H bonds adjacent to a nitrogen atom in amides through decarboxylative cross-coupling of α,β-unsaturated carboxylic acids is reported. A possible reaction mechanism is proposed that involves radical intermediate species. Georg Thieme Verlag Stuttgart, New York.
Phenanthroindolizidine and Related Alkaloids: Synthesis of Tylophorine, Septicine, and Deoxytylophorinine
Cragg, John E.,Herbert, Richard B.,Jackson, Frederick B.,Moody, Christopher J.,Nicolson, Ian T.
, p. 2477 - 2486 (2007/10/02)
Tylophorine (1) is synthesized in two ways.The first method begins with the synthesis of the amide-ester (7), which on reaction, successively, with triethyloxonium fluoroborate and sodium borohydride, gives the aminoester (8) selectively; hydrolysis and polyphosphoric acid-catalysed ring-closure of compound (9) gives the ketone (10) which yields tylophorine (1) on Clemmensen reduction.An alternative approach is by a biogenetically patterned sequence which involves condensation of (3,4-dimethoxybenzoyl)acetic acid (26) with 1-pyrroline (24) generated either in situ from putrescine by pea-seedling diamine oxidase or from ornithine by oxidation with N-bromosuccinimide; the product (16) condenses with 3,4-dimethoxyphenylacetaldehyde in benzene to give an enamine .This undergoes cyclisation and dehydration in methanol; sodium borohydride reduction then gives the alkaloid septicine (19) which, on oxidation with thallium(III) trifluoroacetate, yields tylophorine (1).Deoxytylophorinine (34) is made in an exactly analogous manner to the latter method for tylophorine.
Electroorganic Chemistry. 46. A New Carbon-Carbon Bond Forming Reaction at the α-Position of Amines Utilizing Anodic Oxidation as a Key Step
Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji
, p. 1172 - 1176 (2007/10/02)
A new carbon-carbon bond forming reaction at the α-position of primary and secondary amines has been exploited.The method involves anodic oxidation of urethanes derived from the primary and secondary amines and subsequent acid-catalyzed reaction of the re
