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Theoretical investigation of the selectivity in intramolecular cyclizations of some 2’–aminochalcones to dihydroquinolin–8–ones and indolin–3–ones

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Abstract

The selectivity of the intramolecular cyclizations of a series of 2’–aminochalcones was investigated with an approach that combines spin–polarized conceptual density functional theory and energy calculations. To that aim, condensed–to–atoms electrophilic Fukui functions, f + NN (r), were utilized as descriptors of the proclivity for nucleophilic attack of the NH2 group on the unsaturated α and β carbons. The results of our model are in excellent agreement with the experimental available evidence permitting us in all cases to predict when the cyclization processes led to the formation of 5–exo and 6–endo products.

Understanding the unexpected cyclizations of 2'aminochalcones

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Acknowledgments

AR thanks Universidad Nacional for their financial support (grant 201010018545). EC and PP acknowledges the continuous support from Fondecyt (Chile), Grant Nos. 1100277 (EC) and 1100278 (PP), and from the Universidad Andres Bello (UNAB) through Grant No. DI-219-12/N (Núcleo CIMFQ).

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Authors and Affiliations

  1. Departamento de Quimica, Facultad de Ciencias, Universidad Nacional de Colombia, Av. Cra. 30 No. 45-03, Bogota, Colombia

    Andres Reyes, Paola Andrea Cuervo & Fabian Orozco

  2. Departamento de Quimica. Facultad de Ciencias, Universidad del Valle, AA 25360, Cali, Colombia

    Rodrigo Abonia

  3. Departamento de Ciencias Quimicas. Facultad de Ciencias Exactas, Universidad Andres Bello, Av. Republica 275, 8370146, Santiago, Chile

    Mario Duque-Noreña, Patricia Pérez & Eduardo Chamorro

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  1. Andres Reyes
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  2. Paola Andrea Cuervo
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  3. Fabian Orozco
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  4. Rodrigo Abonia
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  5. Mario Duque-Noreña
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  6. Patricia Pérez
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  7. Eduardo Chamorro
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Correspondence to Andres Reyes or Eduardo Chamorro.

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Fondecyt 1100277, Fondecyt 1100278, DI-UNAB 219-12/N (Nucleo CIMFQ), DIB-UNAL 201010016739

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Reyes, A., Cuervo, P.A., Orozco, F. et al. Theoretical investigation of the selectivity in intramolecular cyclizations of some 2’–aminochalcones to dihydroquinolin–8–ones and indolin–3–ones. J Mol Model 19, 3611–3618 (2013). https://doi.org/10.1007/s00894-013-1893-x

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  • DOI: https://doi.org/10.1007/s00894-013-1893-x

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