Synthesis of New and Highly Functionalized 1,4‐Dihydropyridines and Spirooxindole Dihydropyridines Using L‐Proline as Efficient Catalyst

Abstract

Herein, eco-friendly, mild and efficient synthesis of a new type of 1,4-dihydropyridines and some of the spirooxoindole dihydropyridine derivatives was developed by using L-proline as an effective homogeneous catalyst. The one-pot multicomponent reaction of malononitrile, different anilines, and benzaldehydes were performed in the presence of Water/EtOH (1 : 1) as solvent at 90°C and furnished the corresponding products in high yields. Further, we developed a threecomponent one-pot reaction of malononitrile, anilolactone, and differently substituted isatins to afford new spirooxindole dihydropyridine derivatives using the same catalyst and conditions. All of the obtained products were characterized by spectroscopic and analytical techniques.

Recent advances in the multicomponent synthesis of heterocycles using tetronic acid

“…The use of 20 mol% of L-proline as an effective homogeneous catalyst led to the production of the corresponding products in high yields (Scheme 7). 41 To optimize the synthetic method of the above-mentioned heterocycle structures, a comparative study of a domino, onepot reaction involving 4-nitrobenzaldehyde (2), malononitrile (20), and anilolactones (29) was conducted. An was performed in aqueous ethanol, combining 4-nitrobenzaldehyde (2), malononitrile (20), tetronic acid (1), and three types of aniline (18) in a one-pot reaction using L-proline as a catalyst.…”

Decade Advance of Isatin in Three‐component Reactions

“…As shown in Scheme 38, the preparation of hydropyridine‐fused spirooxindoles 38.1 could be yielded by cyclization of enamines and cyano moiety. Ethylenediamine diacetate (EDDA), [46a] L ‐proline, [46b] and chiral cinchona alkaloid [46e] provided rapid routes to the synthesis of 38.1 . The cinchona alkaloid [46e] ‐catalyzed method focused on the enantioselective transformations, which might be attributed to two hydroxyl groups in this organocatalyst.…”

Loading of g‐C3N4 on Core‐Shell Magnetic Mesoporous Silica Nanospheres as a Solid Base Catalyst for the Green Synthesis of some Chromene Derivatives under Different Conditions

“…In this contribution, this method was thus successfully used to prepare an efficient basic heterogeneous catalyst. The obtained catalyst was employed in the preparation of some dihydropyranochromene and spiro‐dihydropyranochromene derivatives through the environmentally friendly method in green solvents (Scheme 1) which are desirable from the point of green chemistry [26] …”

“…The obtained catalyst was employed in the preparation of some dihydropyranochromene and spiro-dihydropyranochromene derivatives through the environmentally friendly method in green solvents (Scheme 1) which are desirable from the point of green chemistry. [26] Due to special properties of chromene derivatives such as anti-HIV, anti-tuberculosis, antioxidants anti-cancer, antiseptic and anti-inflammatory (in the field of medicinal chemistry), they have attracted much attention in recent years. [27][28][29][30][31][32][33][34][35] Furthermore, the interest in chromenes bearing an additional nitrile functionality arises from their potential application in the treatment of human inflammatory TNFa-mediated diseases, such as rheumatoid and psoriatic arthritis, and in cancer therapy.…”