The β-Csp 3 À H functionalization of N-sulfonyl ketimines with 2-(2-enynl)pyridines/quinolines via a cooperative Ag(I)-/organobase-catalyzed 5-endo-dig cyclization-addition reaction is reported. This successive CÀ N/CÀ C bond-making reaction provides a simple and atom-economical technique for granting a diverse set of 1,3-disubstituted indolizines/ pyrrolo[1,2-a]quinolines possessing a synthetically resourceful N-sulfonyl ketimine moiety. Moreover, our designed strategy applies to broad substrates and allows various functionalities. Furthermore, this technique has many imperative synthetic points such as mild reaction conditions, low catalyst loading, acceptable chemical yields and highly diastereoselective (up to � 93 : 7 dr). The N-sulfonyl ketimine moiety of indolizine was easily transmuted into the reputed classes of coumarin and benzofuran derivatives.
An unprecedented substrate-controlled annulation method for the synthesis of fascinating classes of angularly fused cyclopenta[c]chromenes and benzo[f ]cyclopenta[d][1,2]thiazepine 5,5-dioxide derivatives in good to high chemical yields is reported. This Michael-initiated ring-expansion reaction would enable two C−C and one C−O or C−N bonds by a judicious choice of carbonucleophiles, either 4-alkyl or 3-alkyl-substituted Nsulfonyl ketimines, respectively, with a series of donor−acceptor cyclopropane scaffolds as 4C sources promoted by DBU. Moreover, this eco-friendly method is mild enough to protect different kinds of functionalities. Importantly, the prepared fused fulvene scaffolds were smoothly transformed into a special class of hexahydrocyclopenta[c]chromenes as single cis−cis−cis−cis diastereomers in excellent yields by a simple catalytic hydrogenation reaction.
An interesting desymmetric [3+2] annulation reaction between p-quinamines as prochiral N-donors and 2-aroyl-1-chlorocyclopropanecarboxylates facilitated by base is reported. This successive double Michael reaction delivers a unique class of cyclopropane-fused-hydoindol-5-one frameworks...
A new
metal-, oxidant-, and solvent-free ecofriendly domino method
has been established for modular synthesis of a diverse range of medicinally
promising hydroxyarylated unsymmetrical pyridines in good to high
chemical yields with an excellent regioselectivity. This domino process
involves a range of N-sulfonyl ketimines as C,N-binucleophiles,
enolizable ketones, and aromatic/heteroaromatic aldehydes using ammonium
acetate as an ideal promoter under neat conditions, which creates
two new C–C bonds and one C–N bond. Notably, the neutral
reaction conditions are mild enough to tolerate a range of functionalities
and cover a variety of substrates, thus bestowing a powerful avenue
to access tri- and tetrasubstituted pyridines including carbo- and
heterocyclic fused ones. Interestingly, a practical, scalable, and
high-yielding synthesis of pyridylphenol derivatives was successfully
accomplished by our unique method.
Synthesis of 2-(Substituted aryl)-3-(N 9 -carbazolylacetamidyl)-4oxothiazolidines and Their 5-Arylidene Derivatives as Antifungal Agents.-The title compounds (V) and (VI) are tested as antifungal agents and found to be less efficient than the Standard drug griseofulvin. -(LODHI, R. S.; SRIVASTAVA, S. D.; Indian J. Chem., Sect. B: Org. Chem.
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