{"_id":"42SNMvEYWvTeKfRjc","bibbaseid":"brambilla-pirovano-giannangeli-abbiati-caselli-rossi-goldcatalyzedcascadereactionsof4hfuro32bindoleswithpropargylesterssynthesisof2alkenylidene3oxoindolines-2019","author_short":["Brambilla, E.","Pirovano, V.","Giannangeli, M.","Abbiati, G.","Caselli, A.","Rossi, E."],"bibdata":{"bibtype":"article","type":"article","author":[{"propositions":[],"lastnames":["Brambilla"],"firstnames":["E."],"suffixes":[]},{"propositions":[],"lastnames":["Pirovano"],"firstnames":["V."],"suffixes":[]},{"propositions":[],"lastnames":["Giannangeli"],"firstnames":["M."],"suffixes":[]},{"propositions":[],"lastnames":["Abbiati"],"firstnames":["G."],"suffixes":[]},{"propositions":[],"lastnames":["Caselli"],"firstnames":["A."],"suffixes":[]},{"propositions":[],"lastnames":["Rossi"],"firstnames":["E."],"suffixes":[]}],"title":"Gold-catalyzed cascade reactions of 4: H -furo[3,2- b] indoles with propargyl esters: Synthesis of 2-alkenylidene-3-oxoindolines","journal":"Organic Chemistry Frontiers","year":"2019","volume":"6","number":"17","pages":"3078-3084","doi":"10.1039/c9qo00647h","note":"cited By 10","url":"https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071164726&doi=10.1039%2fc9qo00647h&partnerID=40&md5=3008b4bf1217b5d047b17bba2f0b4018","affiliation":"Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica a. Marchesini, Università Degli Studi di Milano, Via Venezian 21, Milan, 20133, Italy; Dipartimento di Chimica and ISTM-CNR, Università Degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy","abstract":"2-Alkenyliden-indolin-3-ones were synthesised in high yields via a cascade reaction between 4H-furo[3,2-b]indoles and propargyl esters. The cascade sequence involves the initial formation of a gold-carbene species via cationic gold(i) catalysed 1,2-acyloxy migration of properly substituted propargyl esters followed by the addition of gold-carbene to furoindole and successive furan ring-opening affording the final products. The obtained compounds contain an extended π-system linked at the C2 of the indolin-3-ones; they show intense colouration (from yellow to purple) and are characterised by UV measurements. © the Partner Organisations 2019.","keywords":"Catalysis; Esters, Cascade reactions; Cationic gold; Colouration; High yield; Pi systems; Propargyl esters; Synthesised; UV measurements, Gold compounds","references":"Hashmi, A.S.K., Toste, F.D., (2012) Modern Gold Catalyzed Synthesis, , Wiley VCH, Weinheim; Lee, Y.-C., Kumar, K., Waldmann, H., (2018) Angew. Chem., Int. Ed., 57, p. 5212; Mascareñas, J.L., Varela, I., López, F., (2019) Acc. Chem. Res., 522, p. 465; Asiri, A.M., Hashmi, A.S.K., (2016) Chem. Soc. Rev., 45, p. 4471; Wagner, B., Belger, K., Minkler, S., Belting, V., Krause, N., (2016) Pure Appl. Chem., 88, p. 391; Collado, A., Gomez-Suarez, A., Nolan, S.P., (2016) Sustainable Catalysis: With Non-endangered Metals, Part 2, 16, p. 41. , M. North, RSC Green Chemistry Series 39, (RSC) Publishing - Royal Society of Chemistry, London, p; Asiria, A.M., Hashmi, A.S.K., (2016) Chem. Soc. Rev., 45, p. 4471; Debrouwer, W., Heugebaert, T.S.A., Roman, B.I., Stevens, C.V., (2015) Adv. Synth. Catal., 357, p. 2975; Dorel, R., Echavarren, A.M., (2015) Chem. Rev., 115, p. 9028; Zhang, D.-H., Tang, X.-Y., Shi, M., (2014) Acc. Chem. Res., 47, p. 913; Yang, W., Hashmi, A.S.K., (2014) Chem. Soc. Rev., 43, p. 2941; Furstner, A., (2014) Acc. Chem. Res., 47, p. 925; Fang, W., Shi, M., (2018) Chem.-Eur. J., 24, p. 9998; Furstner, A., (2018) Angew. Chem., Int. Ed., 57, p. 4215; Quach, R., Furkert, D.P., Brimble, M.A., (2017) Org. Biomol. Chem., 15, p. 3098; Wang, Q., Shi, M., (2017) Synlett, p. 2230; Pan, F., Shu, C., Ye, L.-W., (2016) Org. Biomol. Chem., 14, p. 9456; Blanc, A., Beneteau, V., Weibel, J.-M., Pale, P., (2016) Org. Biomol. Chem., 14, p. 9184; Wagner, B., Belger, K., Minkler, S., Belting, V., Krause, N., (2016) Pure Appl. Chem., 88, p. 391; Wang, Y., Zhang, L., (2014) Catalytic Cascade Reactions, 4, p. 145. , ed. -F. Xu and W. Wang, John Wiley and Sons, Hoboken, p; Zhang, Y., Luo, T., Yang, Z., (2014) Nat. Prod. Rep., 31, p. 489; Rossi, E., Abbiati, G., Pirovano, V., (2017) Eur. J. Org. Chem., p. 4512; Pirovano, V., (2018) Eur. J. Org. Chem., p. 1925; Pirovano, V., Borri, M., Abbiati, G., Rizzato, S., Rossi, E., (2017) Adv. Synth. Catal., 359, p. 1912; Pirovano, V., Negrato, M., Abbiati, G., Dell'Acqua, M., Rossi, E., (2016) Org. Lett., 18, p. 4798; Rossi, E., Abbiati, G., Dell'Acqua, M., Negrato, M., Paganoni, A., Pirovano, V., (2016) Org. Biomol. Chem., 14, p. 6095; Pirovano, V., Arpini, E., Dell'Acqua, M., Vicente, R., Abbiati, G., Rossi, E., (2016) Adv. Synth. Catal., 358, p. 403; Pirovano, V., Brambilla, E., Rizzato, S., Abbiati, G., Bozzi, M., Rossi, E., (2019) J. Org. Chem., 84, p. 5150; Leboeuf, D., Gaydou, M., Wanga, Y., Echavarren, A.M., (2014) Org. Chem. Front., 1, p. 759; Hashmi, A.S.K., Toste, F.D., (2012) Modern Gold Catalyzed Synthesis, pp. 75-134. , ed. de Mendoza and A. M. Echavarren, Wiley VCH, Weinheim; Wang, S., (2018) Tetrahedron Lett., 59, p. 1317; Day, D.P., Chan, P.W.H., (2016) Adv. Synth. Catal., 358, p. 1368; Ayers, B.J., Chan, P.W.H., (2015) Synlett, p. 1305; Shiroodi, K., Gevorgyan, V., (2013) Chem. Soc. Rev., 42, p. 4991; García-Morales, C., Pei, X.-L., Sarria Toro, J.M., Echavarren, A.M., (2019) Angew. Chem., Int. Ed., 58, p. 3957; Harris, R.J., Widenhoefer, R.A., (2016) Chem. Soc. Rev., 45, p. 4533; Wang, Y., Muratore, M.E., Echavarren, A.M., (2015) Chem.-Eur. J., 21, p. 7332; Shi, X., Gorin, D.J., Toste, F.D., (2005) J. Am. Chem. Soc., 127, p. 5802; Zhao, J., Yang, S., Xie, X., Li, X., Liu, Y., (2018) J. Org. Chem., 83, p. 1287; Mathiew, M., Tan, J.K., Chan, P.W.H., (2018) Angew. Chem., Int. Ed., 57, p. 14235; Chen, X., Day, D.P., Teo, W.T., Chan, P.W.H., (2016) Org. Lett., 18, p. 5936; Bürki, C., Whyte, A., Arndt, S., Hashmi, A.S.K., Lautens, M., (2016) Org. Lett., 18, p. 5058; Susanti, D., Liu, L.-J., Rao, W., Lin, S., Ma, D.-L., Leung, C.-H., Chan, P.W.H., (2015) Chem.-Eur. J., 21, p. 9111; Qian, D., Zhang, J., (2015) Chem. Soc. Rev., 44, p. 677; Shin, S., (2015) Top. Curr. Chem., 357, p. 25; Butin, A.V., Abaev, V.T., Stroganova, T.A., Gutnov, A.V., (2001) Targets in Heterocyclic Systems, 5, p. 131. , ed. O. A. Attanasi and D. Spinelli, Societa Chimica Italiana, Roma, p; Trushkov, I.V., Uchuskin, M.G., Butin, A.V., (2015) Eur. J. Org. Chem., p. 2999; El Kaim, L., Grimaud, L., Wagschal, S., (2011) Chem. Commun., 47, p. 1887; Yin, B., Yu, H., Li, Z., Zhong, W., Gu, W., (2012) Synthesis, p. 3735; Butin, A.V., Uchuskin, M.G., Pilipenko, A.S., Tsiunchik, F.A., Cheshkov, D.A., Trushkov, I.V., (2010) Eur. J. Org. Chem., p. 920; Abaev, V.T., Plieva, A.T., Chalikidi, P.N., Uchuskin, M.G., Trushkov, I.V., Butin, A.V., (2014) Org. Lett., 16, p. 4150; Yin, B., Cai, C., Zeng, G., Zhang, R., Li, X., Jiang, H., (2012) Org. Lett., 14, p. 1098; Muthusamy, S., Azhagan, D., (2011) Tetrahedron Lett., 52, p. 6732; Alves, A.J.S., Lopes, S.M.M., Henriques, M.S.C., Paixão, J.A., Pinho E Melo, T.M.V.D., (2017) Eur. J. Org. Chem., p. 4011; Lopes, S.M.M., Henriques, M.S.C., Paixão, J.A., Pinho E Melo, T.M.V.D., (2015) Eur. J. Org. Chem., p. 6146; Chen, Y., Li, G., Liua, Y., (2011) Adv. Synth. Catal., 353, p. 392; Rao, W., Sally, Berry, S.N., Chan, P.W.H., (2014) Chem.-Eur. J., 20, p. 13174; Petermayer, C., Thumser, S., Kink, F., Mayer, P., Dube, H., (2017) J. Am. Chem. Soc., 139, p. 15060; Dubonosov, A.D., Sitkina, L.M., Bren, V.A., Bushkov, A.Y., Minkin, V.I., (1984) Chem. Heterocycl. Compd., 20, p. 951; Guo, C., Schedler, M., Daniliuc, C.G., Glorius, F., (2014) Angew. Chem., Int. Ed., 53, p. 10232; Flitsch, W., Jones, R.A., Hohenhorst, M., (1987) Tetrahedron Lett., 28, p. 4397; Flitsch, W., Hohenhorst, M., (1990) Liebigs Ann. Chem., p. 449","correspondence_address1":"Brambilla, E.; Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica a. Marchesini, Via Venezian 21, Italy; email: elisa.brambilla@unimi.it","publisher":"Royal Society of Chemistry","issn":"20524110","language":"English","abbrev_source_title":"Org. Chem. Front.","document_type":"Article","source":"Scopus","bibtex":"@ARTICLE{Brambilla20193078,\nauthor={Brambilla, E. and Pirovano, V. and Giannangeli, M. and Abbiati, G. and Caselli, A. and Rossi, E.},\ntitle={Gold-catalyzed cascade reactions of 4: H -furo[3,2- b] indoles with propargyl esters: Synthesis of 2-alkenylidene-3-oxoindolines},\njournal={Organic Chemistry Frontiers},\nyear={2019},\nvolume={6},\nnumber={17},\npages={3078-3084},\ndoi={10.1039/c9qo00647h},\nnote={cited By 10},\nurl={https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071164726&doi=10.1039%2fc9qo00647h&partnerID=40&md5=3008b4bf1217b5d047b17bba2f0b4018},\naffiliation={Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica a. Marchesini, Università Degli Studi di Milano, Via Venezian 21, Milan, 20133, Italy; Dipartimento di Chimica and ISTM-CNR, Università Degli Studi di Milano, Via Golgi 19, Milan, 20133, Italy},\nabstract={2-Alkenyliden-indolin-3-ones were synthesised in high yields via a cascade reaction between 4H-furo[3,2-b]indoles and propargyl esters. The cascade sequence involves the initial formation of a gold-carbene species via cationic gold(i) catalysed 1,2-acyloxy migration of properly substituted propargyl esters followed by the addition of gold-carbene to furoindole and successive furan ring-opening affording the final products. The obtained compounds contain an extended π-system linked at the C2 of the indolin-3-ones; they show intense colouration (from yellow to purple) and are characterised by UV measurements. © the Partner Organisations 2019.},\nkeywords={Catalysis; Esters, Cascade reactions; Cationic gold; Colouration; High yield; Pi systems; Propargyl esters; Synthesised; UV measurements, Gold compounds},\nreferences={Hashmi, A.S.K., Toste, F.D., (2012) Modern Gold Catalyzed Synthesis, , Wiley VCH, Weinheim; Lee, Y.-C., Kumar, K., Waldmann, H., (2018) Angew. Chem., Int. Ed., 57, p. 5212; Mascareñas, J.L., Varela, I., López, F., (2019) Acc. Chem. Res., 522, p. 465; Asiri, A.M., Hashmi, A.S.K., (2016) Chem. Soc. Rev., 45, p. 4471; Wagner, B., Belger, K., Minkler, S., Belting, V., Krause, N., (2016) Pure Appl. Chem., 88, p. 391; Collado, A., Gomez-Suarez, A., Nolan, S.P., (2016) Sustainable Catalysis: With Non-endangered Metals, Part 2, 16, p. 41. , M. North, RSC Green Chemistry Series 39, (RSC) Publishing - Royal Society of Chemistry, London, p; Asiria, A.M., Hashmi, A.S.K., (2016) Chem. Soc. Rev., 45, p. 4471; Debrouwer, W., Heugebaert, T.S.A., Roman, B.I., Stevens, C.V., (2015) Adv. Synth. Catal., 357, p. 2975; Dorel, R., Echavarren, A.M., (2015) Chem. Rev., 115, p. 9028; Zhang, D.-H., Tang, X.-Y., Shi, M., (2014) Acc. Chem. Res., 47, p. 913; Yang, W., Hashmi, A.S.K., (2014) Chem. Soc. Rev., 43, p. 2941; Furstner, A., (2014) Acc. Chem. Res., 47, p. 925; Fang, W., Shi, M., (2018) Chem.-Eur. J., 24, p. 9998; Furstner, A., (2018) Angew. Chem., Int. Ed., 57, p. 4215; Quach, R., Furkert, D.P., Brimble, M.A., (2017) Org. Biomol. Chem., 15, p. 3098; Wang, Q., Shi, M., (2017) Synlett, p. 2230; Pan, F., Shu, C., Ye, L.-W., (2016) Org. Biomol. Chem., 14, p. 9456; Blanc, A., Beneteau, V., Weibel, J.-M., Pale, P., (2016) Org. Biomol. Chem., 14, p. 9184; Wagner, B., Belger, K., Minkler, S., Belting, V., Krause, N., (2016) Pure Appl. Chem., 88, p. 391; Wang, Y., Zhang, L., (2014) Catalytic Cascade Reactions, 4, p. 145. , ed. -F. Xu and W. Wang, John Wiley and Sons, Hoboken, p; Zhang, Y., Luo, T., Yang, Z., (2014) Nat. Prod. Rep., 31, p. 489; Rossi, E., Abbiati, G., Pirovano, V., (2017) Eur. J. Org. Chem., p. 4512; Pirovano, V., (2018) Eur. J. Org. Chem., p. 1925; Pirovano, V., Borri, M., Abbiati, G., Rizzato, S., Rossi, E., (2017) Adv. Synth. Catal., 359, p. 1912; Pirovano, V., Negrato, M., Abbiati, G., Dell'Acqua, M., Rossi, E., (2016) Org. Lett., 18, p. 4798; Rossi, E., Abbiati, G., Dell'Acqua, M., Negrato, M., Paganoni, A., Pirovano, V., (2016) Org. Biomol. Chem., 14, p. 6095; Pirovano, V., Arpini, E., Dell'Acqua, M., Vicente, R., Abbiati, G., Rossi, E., (2016) Adv. Synth. Catal., 358, p. 403; Pirovano, V., Brambilla, E., Rizzato, S., Abbiati, G., Bozzi, M., Rossi, E., (2019) J. Org. Chem., 84, p. 5150; Leboeuf, D., Gaydou, M., Wanga, Y., Echavarren, A.M., (2014) Org. Chem. Front., 1, p. 759; Hashmi, A.S.K., Toste, F.D., (2012) Modern Gold Catalyzed Synthesis, pp. 75-134. , ed. de Mendoza and A. M. Echavarren, Wiley VCH, Weinheim; Wang, S., (2018) Tetrahedron Lett., 59, p. 1317; Day, D.P., Chan, P.W.H., (2016) Adv. Synth. Catal., 358, p. 1368; Ayers, B.J., Chan, P.W.H., (2015) Synlett, p. 1305; Shiroodi, K., Gevorgyan, V., (2013) Chem. Soc. Rev., 42, p. 4991; García-Morales, C., Pei, X.-L., Sarria Toro, J.M., Echavarren, A.M., (2019) Angew. Chem., Int. Ed., 58, p. 3957; Harris, R.J., Widenhoefer, R.A., (2016) Chem. Soc. Rev., 45, p. 4533; Wang, Y., Muratore, M.E., Echavarren, A.M., (2015) Chem.-Eur. J., 21, p. 7332; Shi, X., Gorin, D.J., Toste, F.D., (2005) J. Am. Chem. Soc., 127, p. 5802; Zhao, J., Yang, S., Xie, X., Li, X., Liu, Y., (2018) J. Org. Chem., 83, p. 1287; Mathiew, M., Tan, J.K., Chan, P.W.H., (2018) Angew. Chem., Int. Ed., 57, p. 14235; Chen, X., Day, D.P., Teo, W.T., Chan, P.W.H., (2016) Org. Lett., 18, p. 5936; Bürki, C., Whyte, A., Arndt, S., Hashmi, A.S.K., Lautens, M., (2016) Org. Lett., 18, p. 5058; Susanti, D., Liu, L.-J., Rao, W., Lin, S., Ma, D.-L., Leung, C.-H., Chan, P.W.H., (2015) Chem.-Eur. J., 21, p. 9111; Qian, D., Zhang, J., (2015) Chem. Soc. Rev., 44, p. 677; Shin, S., (2015) Top. Curr. Chem., 357, p. 25; Butin, A.V., Abaev, V.T., Stroganova, T.A., Gutnov, A.V., (2001) Targets in Heterocyclic Systems, 5, p. 131. , ed. O. A. Attanasi and D. Spinelli, Societa Chimica Italiana, Roma, p; Trushkov, I.V., Uchuskin, M.G., Butin, A.V., (2015) Eur. J. Org. Chem., p. 2999; El Kaim, L., Grimaud, L., Wagschal, S., (2011) Chem. Commun., 47, p. 1887; Yin, B., Yu, H., Li, Z., Zhong, W., Gu, W., (2012) Synthesis, p. 3735; Butin, A.V., Uchuskin, M.G., Pilipenko, A.S., Tsiunchik, F.A., Cheshkov, D.A., Trushkov, I.V., (2010) Eur. J. Org. Chem., p. 920; Abaev, V.T., Plieva, A.T., Chalikidi, P.N., Uchuskin, M.G., Trushkov, I.V., Butin, A.V., (2014) Org. Lett., 16, p. 4150; Yin, B., Cai, C., Zeng, G., Zhang, R., Li, X., Jiang, H., (2012) Org. Lett., 14, p. 1098; Muthusamy, S., Azhagan, D., (2011) Tetrahedron Lett., 52, p. 6732; Alves, A.J.S., Lopes, S.M.M., Henriques, M.S.C., Paixão, J.A., Pinho E Melo, T.M.V.D., (2017) Eur. J. Org. Chem., p. 4011; Lopes, S.M.M., Henriques, M.S.C., Paixão, J.A., Pinho E Melo, T.M.V.D., (2015) Eur. J. Org. Chem., p. 6146; Chen, Y., Li, G., Liua, Y., (2011) Adv. Synth. Catal., 353, p. 392; Rao, W., Sally, Berry, S.N., Chan, P.W.H., (2014) Chem.-Eur. J., 20, p. 13174; Petermayer, C., Thumser, S., Kink, F., Mayer, P., Dube, H., (2017) J. Am. Chem. Soc., 139, p. 15060; Dubonosov, A.D., Sitkina, L.M., Bren, V.A., Bushkov, A.Y., Minkin, V.I., (1984) Chem. Heterocycl. Compd., 20, p. 951; Guo, C., Schedler, M., Daniliuc, C.G., Glorius, F., (2014) Angew. Chem., Int. Ed., 53, p. 10232; Flitsch, W., Jones, R.A., Hohenhorst, M., (1987) Tetrahedron Lett., 28, p. 4397; Flitsch, W., Hohenhorst, M., (1990) Liebigs Ann. Chem., p. 449},\ncorrespondence_address1={Brambilla, E.; Dipartimento di Scienze Farmaceutiche-Sezione di Chimica Generale e Organica a. Marchesini, Via Venezian 21, Italy; email: elisa.brambilla@unimi.it},\npublisher={Royal Society of Chemistry},\nissn={20524110},\nlanguage={English},\nabbrev_source_title={Org. Chem. Front.},\ndocument_type={Article},\nsource={Scopus},\n}\n\n","author_short":["Brambilla, E.","Pirovano, V.","Giannangeli, M.","Abbiati, G.","Caselli, A.","Rossi, E."],"key":"Brambilla20193078","id":"Brambilla20193078","bibbaseid":"brambilla-pirovano-giannangeli-abbiati-caselli-rossi-goldcatalyzedcascadereactionsof4hfuro32bindoleswithpropargylesterssynthesisof2alkenylidene3oxoindolines-2019","role":"author","urls":{"Paper":"https://www.scopus.com/inward/record.uri?eid=2-s2.0-85071164726&doi=10.1039%2fc9qo00647h&partnerID=40&md5=3008b4bf1217b5d047b17bba2f0b4018"},"keyword":["Catalysis; Esters","Cascade reactions; Cationic gold; Colouration; High yield; Pi systems; Propargyl esters; Synthesised; UV measurements","Gold compounds"],"metadata":{"authorlinks":{}}},"bibtype":"article","biburl":"https://cloud.alberti.top/index.php/s/xQ8igwraeGLfEPJ/download/scopus.bib","dataSources":["3vf8ATvaZFv2FGt7R","irnS7ryEAzf9jZde2","LBbkvwYBGL2WNBwtp","7pF76B4jHaih5QEAT"],"keywords":["catalysis; esters","cascade reactions; cationic gold; colouration; high yield; pi systems; propargyl esters; synthesised; uv measurements","gold compounds"],"search_terms":["gold","catalyzed","cascade","reactions","furo","indoles","propargyl","esters","synthesis","alkenylidene","oxoindolines","brambilla","pirovano","giannangeli","abbiati","caselli","rossi"],"title":"Gold-catalyzed cascade reactions of 4: H -furo[3,2- b] indoles with propargyl esters: Synthesis of 2-alkenylidene-3-oxoindolines","year":2019}