Synthesis, structure and reactivity of amino-benzodifurane derivatives (430 views)
Comptes Rendus Chimie (ISSN: 1631-0748), 2009 May; 12(5): 622-634.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 1.58, 5-year impact factor: 1.653
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-64749092508&partnerID=40&md5=b0ad1d4914409a9037c5a715dcea4609
Keywords: Amino-Benzodifurane, Polycycles, Polymers, X-Ray Diffraction Structures,
Affiliations:
*** IBB - CNR ***
Dipartimento di Chimica Paolo Corradini, Università degli Studi di Napoli Federico II, Complesso Universitario di Monte S. Angelo, via Cintia, 80126 Napoli, Italy
Dipartimento di Scienza degli Alimenti, Università degli Studi di Napoli Federico II, via Università 100, 80155 Portici, Napoli, Italy
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Napoli, Italy
References:
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., (2007) Bioorg. Med. Chem. Lett., 17, p. 299
Chambers, J.J., Kurrasch-Orbaugh, D.H., Parker, M.A., Nichols, D.E., (2001) J. Med. Chem., 44, p. 1003
Abdul-Aziz, M., Auping, J.V., Meador, M.A., (1995) J. Org. Chem., 60, p. 1303
Daub, J., Beck, M., Knorr, A., Spreitzer, H., (1996) Pure Appl. Chem., 68, p. 1399
Jung, I., Lee, J.K., Song, K., Kang, S.O., Ko, J., (2007) J. Org. Chem., 72, p. 3652
Tsuji, H., Mitsui, C., Ilies, L., Sato, Y., Nakamura, E., (2007) J. Am. Chem. Soc., 129, p. 11902
Qi, X., Li, N., Xu, Q., Lu, J., Wang, L., (2006) High Perform. Polym., 18, p. 519
Craven, R., (1931) J. Chem. Soc., p. 1605
Wood, J.H., Colburn Jr., C.S., Cox, L., Garland, H.C., (1944) J. Am. Chem. Soc., 66, p. 1540
Wood, J.H., Gibson, R.E., (1949) J. Am. Chem. Soc., 71, p. 393
Wood, J.H., Cox, L., (1955) Organic Syntheses, Collective, 3. , Wiley Ed. p. 286
Jeffreys, J.A.D., (1959) J. Chem. Soc., p. 2153
Ogata, N., Sanui, K., Kanasugi, K., Ohira, N., (1975) Polym. J., 7, p. 544
Cheng, L., Greenhalgh, C.W., Griffiths, J., Napier, R.J., Shand, C.A., Thomson, R.H., (1983) J. Chem. Res., Synopses, p. 28
Derkosch, J., Specht, I., (1961) Monatsh. Chem., 92, p. 542
Katritzky, A.R., Derkosch, J., (1962) Monatsh. Chem., 93, p. 541
King, T.J., Newall, C.E., (1965) J. Chem. Soc., p. 974
Obushak, M.D., Martyak, R.L., Matiychuk, V.S., (2002) Pol. J. Chem., 76, p. 1419
Meyer, H.J., Nolde, C., Thomsen, I., Lawesson, S.O., (1978) Bull. Soc. Chim. Belg., 87, p. 621
Beagley, W., Flowers, T., Hafees, A., Pritchard, R.G., (1987) Acta Crystallogr., C43, p. 1971
Polson, M.I.J., Steel, P.J., (2006) Acta Crystallogr., E62, pp. o1300
Steglich, W., Jeschke, R., Buschmann, E., (1986) Gazz. Chim. Ital., 116, p. 361
Shariat, M., Abdollahi, S., (2004) Molecules, 9, p. 705
Papadopulos, E.P., Torres, C.D., (1982) Heterocycles, 19, p. 1039
Ming, Y., Horlemann, N., Wamhoff, H., (1987) Chem. Ber., 120, p. 1427
Kennedy, A.R., Kalhaf, A.I., (1997) Acta Crystallogr., C53, p. 744
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Spagna, R., (1999) J. Appl. Crystallogr., 32, p. 115
Sheldrick, G.M., (1997) SHELXL-97 Program, , SHELX-97, University of Göttingen, Germany
Chambers, J. J., Kurrasch-Orbaugh, D. H., Parker, M. A., Nichols, D. E., (2001) J. Med. Chem., 44, p. 1003
Jung, I., Lee, J. K., Song, K., Kang, S. O., Ko, J., (2007) J. Org. Chem., 72, p. 3652
Wood, J. H., Colburn Jr., C. S., Cox, L., Garland, H. C., (1944) J. Am. Chem. Soc., 66, p. 1540
Wood, J. H., Gibson, R. E., (1949) J. Am. Chem. Soc., 71, p. 393
Wood, J. H., Cox, L., (1955) Organic Syntheses, Collective, 3. , Wiley Ed. p. 286
Jeffreys, J. A. D., (1959) J. Chem. Soc., p. 2153
Katritzky, A. R., Derkosch, J., (1962) Monatsh. Chem., 93, p. 541
King, T. J., Newall, C. E., (1965) J. Chem. Soc., p. 974
Obushak, M. D., Martyak, R. L., Matiychuk, V. S., (2002) Pol. J. Chem., 76, p. 1419
Meyer, H. J., Nolde, C., Thomsen, I., Lawesson, S. O., (1978) Bull. Soc. Chim. Belg., 87, p. 621
Polson, M. I. J., Steel, P. J., (2006) Acta Crystallogr., E62, pp. o1300
Papadopulos, E. P., Torres, C. D., (1982) Heterocycles, 19, p. 1039
Kennedy, A. R., Kalhaf, A. I., (1997) Acta Crystallogr., C53, p. 744
Sheldrick, G. M., (1997) SHELXL-97 Program, , SHELX-97, University of G ttingen, Germany
Comptes Rendus Chimie (ISSN: 1631-0748), 2009 May; 12(5): 622-634.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 1.58, 5-year impact factor: 1.653
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-64749092508&partnerID=40&md5=b0ad1d4914409a9037c5a715dcea4609
Keywords: Amino-Benzodifurane, Polycycles, Polymers, X-Ray Diffraction Structures,
Affiliations:
*** IBB - CNR ***
Dipartimento di Chimica Paolo Corradini, Università degli Studi di Napoli Federico II, Complesso Universitario di Monte S. Angelo, via Cintia, 80126 Napoli, Italy
Dipartimento di Scienza degli Alimenti, Università degli Studi di Napoli Federico II, via Università 100, 80155 Portici, Napoli, Italy
Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Napoli, Italy
References:
Feng, Z., Mohapatra, S., Klimko, P.G., Hellberg, M.R., May, J.A., Kelly, C., Williams, G., Sharif, N.A., (2007) Bioorg. Med. Chem. Lett., 17, p. 299
Chambers, J.J., Kurrasch-Orbaugh, D.H., Parker, M.A., Nichols, D.E., (2001) J. Med. Chem., 44, p. 1003
Abdul-Aziz, M., Auping, J.V., Meador, M.A., (1995) J. Org. Chem., 60, p. 1303
Daub, J., Beck, M., Knorr, A., Spreitzer, H., (1996) Pure Appl. Chem., 68, p. 1399
Jung, I., Lee, J.K., Song, K., Kang, S.O., Ko, J., (2007) J. Org. Chem., 72, p. 3652
Tsuji, H., Mitsui, C., Ilies, L., Sato, Y., Nakamura, E., (2007) J. Am. Chem. Soc., 129, p. 11902
Qi, X., Li, N., Xu, Q., Lu, J., Wang, L., (2006) High Perform. Polym., 18, p. 519
Craven, R., (1931) J. Chem. Soc., p. 1605
Wood, J.H., Colburn Jr., C.S., Cox, L., Garland, H.C., (1944) J. Am. Chem. Soc., 66, p. 1540
Wood, J.H., Gibson, R.E., (1949) J. Am. Chem. Soc., 71, p. 393
Wood, J.H., Cox, L., (1955) Organic Syntheses, Collective, 3. , Wiley Ed. p. 286
Jeffreys, J.A.D., (1959) J. Chem. Soc., p. 2153
Ogata, N., Sanui, K., Kanasugi, K., Ohira, N., (1975) Polym. J., 7, p. 544
Cheng, L., Greenhalgh, C.W., Griffiths, J., Napier, R.J., Shand, C.A., Thomson, R.H., (1983) J. Chem. Res., Synopses, p. 28
Derkosch, J., Specht, I., (1961) Monatsh. Chem., 92, p. 542
Katritzky, A.R., Derkosch, J., (1962) Monatsh. Chem., 93, p. 541
King, T.J., Newall, C.E., (1965) J. Chem. Soc., p. 974
Obushak, M.D., Martyak, R.L., Matiychuk, V.S., (2002) Pol. J. Chem., 76, p. 1419
Meyer, H.J., Nolde, C., Thomsen, I., Lawesson, S.O., (1978) Bull. Soc. Chim. Belg., 87, p. 621
Beagley, W., Flowers, T., Hafees, A., Pritchard, R.G., (1987) Acta Crystallogr., C43, p. 1971
Polson, M.I.J., Steel, P.J., (2006) Acta Crystallogr., E62, pp. o1300
Steglich, W., Jeschke, R., Buschmann, E., (1986) Gazz. Chim. Ital., 116, p. 361
Shariat, M., Abdollahi, S., (2004) Molecules, 9, p. 705
Papadopulos, E.P., Torres, C.D., (1982) Heterocycles, 19, p. 1039
Ming, Y., Horlemann, N., Wamhoff, H., (1987) Chem. Ber., 120, p. 1427
Kennedy, A.R., Kalhaf, A.I., (1997) Acta Crystallogr., C53, p. 744
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G., Spagna, R., (1999) J. Appl. Crystallogr., 32, p. 115
Sheldrick, G.M., (1997) SHELXL-97 Program, , SHELX-97, University of Göttingen, Germany
Chambers, J. J., Kurrasch-Orbaugh, D. H., Parker, M. A., Nichols, D. E., (2001) J. Med. Chem., 44, p. 1003
Jung, I., Lee, J. K., Song, K., Kang, S. O., Ko, J., (2007) J. Org. Chem., 72, p. 3652
Wood, J. H., Colburn Jr., C. S., Cox, L., Garland, H. C., (1944) J. Am. Chem. Soc., 66, p. 1540
Wood, J. H., Gibson, R. E., (1949) J. Am. Chem. Soc., 71, p. 393
Wood, J. H., Cox, L., (1955) Organic Syntheses, Collective, 3. , Wiley Ed. p. 286
Jeffreys, J. A. D., (1959) J. Chem. Soc., p. 2153
Katritzky, A. R., Derkosch, J., (1962) Monatsh. Chem., 93, p. 541
King, T. J., Newall, C. E., (1965) J. Chem. Soc., p. 974
Obushak, M. D., Martyak, R. L., Matiychuk, V. S., (2002) Pol. J. Chem., 76, p. 1419
Meyer, H. J., Nolde, C., Thomsen, I., Lawesson, S. O., (1978) Bull. Soc. Chim. Belg., 87, p. 621
Polson, M. I. J., Steel, P. J., (2006) Acta Crystallogr., E62, pp. o1300
Papadopulos, E. P., Torres, C. D., (1982) Heterocycles, 19, p. 1039
Kennedy, A. R., Kalhaf, A. I., (1997) Acta Crystallogr., C53, p. 744
Sheldrick, G. M., (1997) SHELXL-97 Program, , SHELX-97, University of G ttingen, Germany
Synthesis, structure and reactivity of amino-benzodifurane derivatives
The reactivity of amino groups of some dialkyl esters of 2,6-diamino-benzo[1,2-b:4.5-b']difuran-3,7-dicarboxylic acid towards acylic reactants was investigated. The easy and chemoselective obtainment of the N,N'-acetyl- and N,N'-benzoyl-derivatives makes the diamino compounds suitable monomers to prepare polymers with tunable chemo-physical behavior. Two novel polyamides, potentially useful for applications in the field of organic electronics, were synthesized and their properties examined. Single crystal X-ray analysis was performed on some of the prepared compounds, thus obtaining information on the extent of electronic conjugation. The obtainment of an oxazinone derivative by cyclization reaction of an N,N'-benzoyl ester was also described. To cite this article: U. Caruso et al., C. R. Chimie 12 (2009). (C) 2008 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
The reactivity of amino groups of some dialkyl esters of 2,6-diamino-benzo[1,2-b:4.5-b']difuran-3,7-dicarboxylic acid towards acylic reactants was investigated. The easy and chemoselective obtainment of the N,N'-acetyl- and N,N'-benzoyl-derivatives makes the diamino compounds suitable monomers to prepare polymers with tunable chemo-physical behavior. Two novel polyamides, potentially useful for applications in the field of organic electronics, were synthesized and their properties examined. Single crystal X-ray analysis was performed on some of the prepared compounds, thus obtaining information on the extent of electronic conjugation. The obtainment of an oxazinone derivative by cyclization reaction of an N,N'-benzoyl ester was also described. To cite this article: U. Caruso et al., C. R. Chimie 12 (2009). (C) 2008 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Synthesis, structure and reactivity of amino-benzodifurane derivatives
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