Cyclic enaminones. Part I: stereocontrolled synthesis using diastereoselective and catalytic asymmetric methods

Chattopadhyay, Amit Kumar; Hanessian, Stephen

doi:10.1039/c5cc05891k

Cited by 58 publications

(29 citation statements)

References 81 publications

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“…[2][3][4][5][6][7][8] A privileged status among them have cyclic enaminones and their derivatives. 9,10 They can, in principle, be divided into three structural types I-III (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

Brož¹,

Růžičková²,

Šimůnek³

2016

Arkivoc

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A simple methodology for [1,2-a]-fused tricyclic dihydroquinolines is established. The key step of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitable halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitriles with various ring size (from five-to seven-membered). Optimal reaction conditions (palladium source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of the tricyclic product. A treatment of the products with perchloric acid gives respective quinolinium perchlorates.

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“…[2][3][4][5][6][7][8] A privileged status among them have cyclic enaminones and their derivatives. 9,10 They can, in principle, be divided into three structural types I-III (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

Brož¹,

Růžičková²,

Šimůnek³

2016

Arkivoc

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“…Solid State Chem. 232 (2015) ions at 570 nm. The emission color of the as-prepared phosphors can be tuned from blue to yellow-green by adjusting the Mn 2+ concentration.…”

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confidence: 99%

“…232 (2015) 73-78, http://dx.doi.org/10.1016/j.jssc. 2015 is prepared by calcination of a stoichiometric mixture of SrCO 3 and Ir in air followed by annealing (1. 650-800 C staged heating, 24 h per stage, 2.…”

mentioning

confidence: 99%

“…-(ZHEN, N.; WU, K.; LI*, Q.; PAN, S.; GAO, W.; YANG, Z.; New J. Chem. 39 (2015) 11, 8866-8873, http://dx.doi.org/10.1039/C5NJ01911G ; Sch. Phys.…”

mentioning

confidence: 99%

“…Solid State Chem. 232 (2015) (II) are prepared by solid state reaction of appropriate mixtures of MgO, MgF 2 , and SiO 2 (evacuated silica tubes, 950 C, 30 h; cooling to 300 C at a rate of 2 C/h). Compound (I) crystallizes in the monoclinic space group P2 1 /c (Z = 2, single crystal XRD) and (II) crystallizes in the orthorhombic space group Pnma (Z = 4).…”

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confidence: 99%

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All in One ‐ Complete Issue: ChemInform 1/2016

2016

ChemInform

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Substrate‐Controlled Divergent Synthesis of Enaminones and Pyrroles from Indolizines and Nitroso Compounds

González-Soria

Alonso

2019

Adv Synth Catal

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It is imperative to learn new synthetic transformations to succeed in drug discovery and development. We report the substrate-driven synthesis of β-enaminones and N-aryl pyrroles from indolizines and nitrosoarenes; aryl-substituted indolizines lead to β-enaminones in a regio-and diastereoselective manner, whereas alkyl-substituted indolizines produce tetrasubstituted pyrroles. All products contain a pyridine unit, the second most abundant ring (after phenyl) in the FDA Orange Book. In both cases, the reactions proceed at room temperature without any catalyst. Moreover, both types of products can be obtained in one pot from commercial materials as well as at a gram scale. It is worthy of note that the regioselectivity of the βenaminones is inaccessible by the standard literature methods and their utility has been exemplified in the synthesis of diverse heterocycles. We have made every endeavor to put forward the corresponding reaction mechanisms based on thorough experimental work.

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Cyclic enaminones. Part I: stereocontrolled synthesis using diastereoselective and catalytic asymmetric methods

Cited by 58 publications

References 81 publications

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

Synthesis of [1,2-a]-fused tricyclic dihydroquinolines by palladium-catalyzed intramolecular C–N cross-coupling of polarized heterocyclic enamines

All in One ‐ Complete Issue: ChemInform 1/2016

Substrate‐Controlled Divergent Synthesis of Enaminones and Pyrroles from Indolizines and Nitroso Compounds

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