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Journal ArticleDOI

Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction

28 Jan 2012-Tetrahedron (Elsevier Limited)-Vol. 68, Iss: 4, pp 1321-1329
TL;DR: In this article, a variety of functionalized flavanone derivatives and tetrahydropyrimidine derivatives were achieved under remarkably mild conditions and the combination of good to excellent yields, a simple work-up, and the high compatibility of functional groups makes this an attractive synthetic approach to access flavanones and tetrahedropyridine derivatives.
About: This article is published in Tetrahedron.The article was published on 2012-01-28. It has received 49 citations till now. The article focuses on the topics: Flavanone & Mannich reaction.
Citations
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Journal ArticleDOI
TL;DR: This Perspective highlights advances made by the laboratory since the inception of the photoredox/Ni cross-coupling of benzyltrifluoroborates with aryl bromides and the net C–H functionalization of the radical partner in an effort to improve atom economy.
Abstract: Photoredox catalysis has experienced a revitalized interest from the synthesis community during the past decade. For example, photoredox/Ni dual catalysis protocols have been developed to overcome several inherent limitations of palladium-catalyzed cross-couplings by invoking a single-electron transmetalation pathway. This Perspective highlights advances made by our laboratory since the inception of the photoredox/Ni cross-coupling of benzyltrifluoroborates with aryl bromides. In addition to broadening the scope of trifluoroborate coupling partners, research using readily oxidized hypervalent silicates as radical precursors that demonstrate functional group compatibility is highlighted. The pursuit of electrophilic coupling partners beyond (hetero)aryl bromides has also led to the incorporation of several new classes of C(sp2)-hybridized substrates into light-mediated cross-coupling. Advances to expand the radical toolbox by utilizing feedstock chemicals (e.g., aldehydes) to access radicals that were prev...

394 citations

Journal ArticleDOI
TL;DR: The synergistic effect of the combined use of MCRs and molecular iodine for the development of new eco-compatible methodologies for organic chemistry is highlighted.
Abstract: The multicomponent reactions (MCRs) consist of two or more synthetic steps which are carried out without isolation of any intermediate thus reducing time, saving money, energy and raw materials. The development of MCRs in the presence of molecular iodine is an efficient approach that meets with the requirements of sustainable chemistry. The aim of this review is to highlight the synergistic effect of the combined use of MCRs and molecular iodine for the development of new eco-compatible methodologies for organic chemistry.

158 citations

Journal ArticleDOI
03 Jul 2018
TL;DR: An efficient, green, and sustainable synthesis of new hybrid molecules containing flavanone with triazole by merging the Michael addition and Click reaction using a copper oxide/reduced graphene oxide nanocomposite in one pot is reported.
Abstract: An efficient, green, and sustainable synthesis of new hybrid molecules containing flavanone with triazole by merging the Michael addition and Click reaction using a copper oxide/reduced graphene oxide nanocomposite in one pot is reported. The catalyst can easily be recycled and reused in seven consecutive runs without compromising the product yields. Other notable advantages include using water as a reaction medium and obtaining good to excellent yields, low catalyst loading, high atom efficiency, high substrate variation, and good results in the gram scale reaction.

59 citations

Journal ArticleDOI
TL;DR: In this article, a form of hydromagnesite (HM) with a thin-sheet morphology was synthesized by an environmentally benign approach using simple conventional heating at moderate temperature without using any template in water as medium.
Abstract: A form of hydromagnesite (HM) with flower-like thin-sheet morphology was synthesized by an environmentally benign approach using simple conventional heating at moderate temperature without using any template in water as medium. The versatility of this HM catalyst was studied in the synthesis of flavanones, flavonols and the multicomponent synthesis of 1,4-dihydropyridines in water. The recyclability of catalyst was studied for six times and there was no appreciable loss in its catalytic activity.

49 citations

Journal ArticleDOI
TL;DR: The newly reported trifluoroboratochromanones can be easily accessed from the corresponding chromones on multigram scale and represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.

49 citations

References
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Journal ArticleDOI
TL;DR: Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
Abstract: Chiral nitrogen-containing compounds are widely distributed in nature and include many biologically important molecules (Chart 1). In these compounds, the nitrogen-containing units are known to play important roles for their bioactivities. For the synthesis of these chiral nitrogen-containing building blocks, use of imines as electrophiles is the most promising and convenient route.1 While many approaches using chiral imines or chiral nucleophiles have been reported,1 these diastereoselective reactions have some disadvantages. First, the procedures to introduce chiral auxiliaries to substrates and to remove them after the diastereoselective reactions are often tedious. Second, more than stoichiometric amounts of chiral sources are needed to obtain chiral compounds according to these reactions. On the other hand, catalytic enantioselective reactions provide the most efficient methods for the synthesis of chiral compounds,2 because large quantities of chiral compounds are expected to be prepared using small amounts of chiral sources. While much progress has been made recently in catalytic enantioselective reactions of aldehydes and ketones such as aldol,3 allylation,4 Diels-Alder,5 cyanation reactions,6 reduction,1b,2b etc., progress in catalytic enantioselective reactions of imines is rather slow. There are some difficulties in performing catalytic enantioselective reactions of imines. For example, in the cases of chiral Lewis acid promoted asymmetric Shū Kobayashi was born in 1959 in Tokyo, Japan. He studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama). After spending 11 years at Science University of Tokyo (SUT), he moved to Graduate School of Pharmaceutical Sciences, University of Tokyo, in 1998. His research interests include development of new synthetic methods, development of novel catalysts (especially chiral catalysts), organic synthesis in water, solid-phase organic synthesis, total synthesis of biologically interesting compounds, and organometallic chemistry. He received the first Springer Award in Organometallic Chemistry in 1997.

1,356 citations

Journal ArticleDOI
TL;DR: Modern variants of the Mannich reaction that expand the potential of the classical intermolecular reaction significantly and enable efficient control of the regioselectivities and stereoselectivity are therefore the topic of intensive research.
Abstract: Important building blocks for the synthesis of drugs or natural products are found in Mannich bases and their derivatives Modern variants of the Mannich reaction that expand the potential of the classical intermolecular reaction significantly and enable efficient control of the regioselectivity and stereoselectivity are therefore the topic of intensive research Intramolecular reactions, in particular as part of domino reaction sequences, often afford astoundingly simple and elegant approaches to complex target compounds

967 citations

Journal ArticleDOI
TL;DR: The direct catalytic asymmetric addition of unmodified carbonyl compounds to preformed or in situ-generated imines has emerged as a promising new route to optically enriched alpha- and beta-amino acid derivatives, beta-lactams, and 1,2- and gamma-aminos alcohols.
Abstract: The direct catalytic asymmetric addition of unmodified carbonyl compounds to preformed or in situ-generated imines has emerged as a promising new route to optically enriched alpha- and beta-amino acid derivatives, beta-lactams, and 1,2- and gamma-amino alcohols. The direct catalytic asymmetric Mannich reactions are mediated by small organometallic and organic amine catalysts that can achieve levels of selectivity similar to those possible with natural enzymes. The different small-molecule catalysts described here are complementary in their applications. They also complement each other in syn or anti selectivity of the direct asymmetric Mannich reaction. In this Account, we highlight the recent developments in and contributions to this research.

641 citations

Journal ArticleDOI
01 Sep 2006-Synlett
TL;DR: Iodine is a universal oxidizing agent, especially for the oxidation of alcohols and aldehydes to esters, nitriles and amides as mentioned in this paper, and its use in protecting groups, deprotection, iodocyclization, C-C bond formation, and formation of heterocycles.
Abstract: The synthetic use of molecular iodine is described. Iodine is a universal oxidizing agent, especially for the oxidation of alcohols and aldehydes to esters, nitriles and amides. Further applications are the introduction of protecting groups, deprotection, iodocyclization, C-C bond formation, and formation of heterocycles.

369 citations

Journal ArticleDOI
TL;DR: In this paper, a simple, inexpensive and efficient one-pot synthesis of 1,4-dihydropyridine derivatives at room temperature using catalytic amount of iodine was reported with excellent product yields.

297 citations