Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization
We have developed a metal- and oxidant-free approach to structurally diverse synthesis of benzosultams from aryl sulfonamides through an electrochemical cyclization. Upon variation of the ortho substituent on aryl sulfonamides, five-, six-, and seven-memb
Intramolecular NC rearrangements involving sulfonamide protecting groups
The reaction of amine derivatives orthogonally protected with an aryl sulfonamide and a carbamate, via a base-mediated nitrogen to carbon rearrangement is reported. This noteworthy isomerisation has implications for the use of sulfonamide protecting group
Saidykhan, Amie,Bowen, Richard D.,Gallagher, Richard T.,Martin, William H.C.
supporting information
p. 66 - 68
(2015/02/02)
Synthesis of nitromethyl-substituted oxindole derivatives via a desulfonylation cascade
A cascade reaction giving nitromethyl-substituted oxindole derivatives was developed. The reaction used NaNO2 as the nitro source and potassium peroxydisulfate as an oxidant. This reaction proceeded via a radical mechanism involving substitution-desulfonlylation-cyclization steps in one pot and afforded good yields under mild conditions without using toxic metal catalysts. The resultant nitromethyl-substituted oxindole derivatives are convenient and valuable structures for different derivative syntheses.
N-alkylation of sulfonamides with alcohols by Tf2O
N-sulfonylpyrrolidines and N-alkyl sulfonamides were efficiently prepared via alkylation of sulfonamides with 1,4- diols or alcohols by Tf2O. The reaction occurred under mild reaction conditions in moderate to high yields and tolerated aryl and aliphatic sulfonamides.
Yu, Ting Ting,Qi, Lan-Jun,Cui, Dong-Mei,Zhang, Chen,Zhao, Yan
supporting information
p. 610 - 612
(2015/08/04)
Br?nsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents
N-Alkylation of sulfonamides using cyclic ethers as alkylation reagents and Br?nsted acid as a catalyst produced pyrrolidine and piperidine derivatives in good yields. When using symmetrical and unsymmetrical ethers as alkylation reagents, mono-N-alkylation of sulfonamides took place to afford the corresponding products.
Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide
The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.
Moriyama, Katsuhiko,Nakamura, Yu,Togo, Hideo
supporting information
p. 3812 - 3815
(2014/08/05)
Phase-Transfer-Catalysed N-Alkylation of Carboxamides and Sulfonamides
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Gajda, Tadeusz,Zwierzak, Andrzej
p. 1005 - 1008
(2007/10/02)
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