Exploring the peri- and stereo- selectivities of the cycloaddition reaction of 2-(2- dimethylaminovinyl)-1-benzopyran-4-one with N-phenylmaleimide (NPM) and dimethylacetylenedicarboxylate (DMAD) - A DFT study

Pedraza-Chaverri, 2008, Medicinal properties of mangosteen (Garcinia mangostana), Food Chem. Toxicol., 46, 3227, 10.1016/j.fct.2008.07.024 Gutierrez-Orozco, 2013, Biological activities and bioavailability of mangosteen xanthones: a critical review of the current evidence, Nutrients, 5, 3163, 10.3390/nu5083163 Otrubova, 2018, A novel entry to xanthones by an intramolecular Diels-Alder reaction involving 2-(1,2-dichlorovinyloxy) aryl dienones, Tetrahedron, 74, 5715, 10.1016/j.tet.2018.08.007 Kurniawan, 2021, An update on the anticancer activity of xanthone derivatives: a review, Pharmaceuticals, 14, 1144, 10.3390/ph14111144 Sousa, 2005, Synthesis of xanthones: an overview, Curr. Med. Chem., 12, 2447, 10.2174/092986705774370736 Grover, 1955, Xanthones. Part IV. A new synthesis of hydroxyxanthones and hydroxybenzophenones, J. Chem. Soc., 3982, 10.1039/jr9550003982 Mehta, 1954, Synthetical experiments in the benzopyrone series. A synthesis of 6-methylisoflavones, J. Chem. Soc., 3823, 10.1039/jr9540003823 Olah, 2003, 621 Prakash, 2005, Aroylation of aromatics with aryl carboxylic acids over Nafion-H (polymeric perfluoroalkanesulfonic acid), an environmentally friendly solid acid catalyst: commemorative Issue in Honor of Prof. P. T. Narasimhan on the occasion of his 75th anniversary, Arch. Organ. Chem., 8, 103 Miguel, 2012, Routes to xanthones: an update on the synthetic approaches, Curr. Org. Chem., 16, 2818, 10.2174/138527212804546921 D Locksley, 1966, Extractives from guttiferae. Part IV. Isolation and structure of ugaxanthone and mbarraxanthone from Symphonia globulifera L, J. Chem. Soc. C, 2265, 10.1039/j39660002265 Bennett, 1989, Xanthones from guttiferae, Phytochemistry, 28, 967, 10.1016/0031-9422(89)80170-0 Moreau, 2002, 2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species, Eur. J. Med. Chem., 37, 237, 10.1016/S0223-5234(01)01332-0 Santos, 2017, An overview of 2-styrylchromones: natural occurrence, synthesis, reactivity and biological properties, Eur. J. Org Chem., 3115, 10.1002/ejoc.201700003 Mustafa, 1956, 2-Styrylchromones in the diene synthesis, J. Org. Chem., 21, 849, 10.1021/jo01114a006 Ghosh, 1997, Unusual condensation of 2-(2-dimethylaminovinyl)-1-benzopyran-4-one with dimethyl acetylenedicarboxylate: formation of 2,3-bis(methoxycarbonyl)xanthen-9-one, J. Chem. Soc., Perkin Trans., 1, 2167, 10.1039/a703495d Neochoritis, 2014, Dimethyl acetylenedicarboxylate: a versatile tool in organic synthesis, Synthesis, 46, 537, 10.1055/s-0033-1340615 Wolinsky, 1970, Diels-Alder reaction of acetoxy-1,3-dienes with dimethyl acetylenedicarboxylate and chloromaleic anhydride. Synthesis of benzene derivatives, J. Org. Chem., 35, 3205, 10.1021/jo00835a002 Tanimoto, 1977, A Facile preparation of aromatic carboxylic acid esters by the reaction of 1,3-butadienylamine and 1,3-tubadienyl ether with aceetylene carboxylic acid esters, Tetrahedron Lett., 18, 2899, 10.1016/S0040-4039(01)83105-1 Ghosh, 1999, Benzopyrans. Part 41. Reactions of 2-(2-dimethylaminovinyl)-1-benzopyran-4-ones with various dienophiles, J. Chem. Soc., Perkin Trans., 1, 3005, 10.1039/a903145f Ofori, 2021, A DFT study of the double (3 + 2) cycloaddition of nitrile oxides and allenoates for the formation of spirobiisoxazolines, J. Mol. Graph. Model., 109, 10.1016/j.jmgm.2021.108033 Baffour Pipim, 2021, Computational exploration of the 1,3-dipolar cycloaddition reaction of 7-isopropylidenebenzonorbornadiene with nitrile oxide and cyclic nitrone derivatives, J. Phys. Org. Chem., 34, 10.1002/poc.4174 Pipim, 2020, Investigating the regio-, stereo-, and enantio-selectivities of the 1,3-dipolar cycloaddition reaction of C-cyclopropyl-N-phenylnitrone derivatives and benzylidenecyclopropane derivatives: a DFT study, J. Mol. Graph. Model., 100, 10.1016/j.jmgm.2020.107672 Opoku, 2019, Computational studies on [4 + 2]/[3 + 2] tandem sequential cycloaddition reactions of functionalized acetylenes with cyclopentadiene and diazoalkane for the formation of norbornene pyrazolines, J. Mol. Model., 25, 1 Atta-Kumi, 2021, Investigating the site-, regio-, and stereo-selectivities of the reactions between organic azide and 7-heteronorbornadiene: a DFT mechanistic study, J. Mol. Model., 27, 248, 10.1007/s00894-021-04857-3 Pipim, 2020, (3 + 2) cycloaddition reaction of 7-isopropylidenebenzonorbornadiene and diazomethane derivatives: a theoretical study, J. Mol. Graph. Model., 101, 10.1016/j.jmgm.2020.107713 Raghayachari, 1989, Highly correlated systems. Excitation energies of first row transition metals Sc-Cu, J. Chem. Phys., 91, 1062, 10.1063/1.457230 Watchers, 1970, Gaussian basis set for molecular wavefunctions containing third-row atoms, J. Chem. Phys., 52, 1033, 10.1063/1.1673095 Hay, 1977, Gaussian basis sets for molecular calculations. The representation of 3d orbitals in transition-metal atoms, J. Chem. Phys., 66, 4377, 10.1063/1.433731 Frisch, 2015 Zhao, 2008, Density functionals with broad applicability in chemistry, Acc. Chem. Res., 41, 157, 10.1021/ar700111a Domingo, 2002, Quantitative characterization of the local electrophilicity of organic molecules. Understanding the regioselectivity on Diels-Alder reactions, J. Phys. Chem. A, 106, 6871, 10.1021/jp020715j Parr, 1999, Electrophilicity index, J. Am. Chem. Soc., 121, 1922, 10.1021/ja983494x Koopmans, 1934, Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms, Physica, 1, 104, 10.1016/S0031-8914(34)90011-2 Domingo, 2008, Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study, J. Org. Chem., 73, 4615, 10.1021/jo800572a Ranck, 2001, Modern physical chemistry: a molecular approach, J Chem. Educ., 78, 1024, 10.1021/ed078p1024 Morales-Bayuelo, 2014, Understanding the polar character trend in a series of diels-alder reactions using molecular quantum similarity and chemical reactivity descriptors, Journal of Quantum Chemistry, 1