Abstract
Structural elucidation of the dihydro derivatives obtained as by-products in the classic salt method synthesis of pyrrolo[2,1-a]phthalazines and acetylenic dipolarophiles was achieved by X-ray diffraction analysis of a representative compound. In addition, new pyrrolo[2,1-a]phthalazines were obtained by a one-pot three-component reaction that avoids the formation of the dihydro derivative intermediates.
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Dorweiler C, Holderbaum M, Munzmay T, Spang P, Durr H, Kruger C, Raabe E (1988) Chem Ber 121:843
Cheng Y, Ma B, Wudl F (1999) J Mater Chem 9:2183
Mitsumori T, Bendikov M, Sedó J, Wudl F (2003) Chem Mater 15:3759
Uff BC, Ghaem-Maghami G, Budhram RS, Wilson CL, Apatu JO (1989) J Heterocycl Chem 26:571
Galin FZ, Sakhautdinov IM, Tukhavatullin OR (2007) Russ Chem Bull Int Ed 53:2305
Siriwardana AI, Nakamura I, Yamamoto Y (2004) J Org Chem 69:3202
Komatsu M, Kasano Y, Yamaoka S, Minakata S (2003) Synthesis 35(9):1398
Bridge AW, Hursthouse MB, Lehmann CW, Lythgoe DJ, Newton CG (1993) J Chem Soc Perkin Trans 1:1839
Potts KT, Bordeaux KG, Kuehnling WR, Salsbury RL (1985) J Org Chem 50:1677
Zugrăvescu I, Petrovanu M (1976) N-Ylid chemistry. McGraw-Hill, New York, p 239
Khlebnikov AF, Kostik EI, Kostikov RR (1993) Synthesis 25(6):568
Zhou J, Hu Y, Hu H (2000) J Heterocycl Chem 37:1165
Butnariu RM, Caprosu MD, Bejan V, Ungureanu M, Poiata A, Tuchilus C, Florescu M, Mangalagiu I (2007) J Heterocycl Chem 44:1
Caprosu MC, Zbancioc GN, Moldoveanu CC, Mangalagiu I (2004) Collect Czech Chem Commun 69:426
Dumitrascu F, Mitan CI, Draghici C, Caproiu MT, Raileanu D (2001) Tetrahedron Lett 42:8379
Dumitrascu F, Draghici C, Caproiu MT, Dumitrescu D, Badoiu A (2006) Rev Roum Chim 51:643
Dumitrascu F, Caira MR, Draghici C, Caproiu MT, Barbu L (2009) Rev Chim (Bucharest) 60:851
Sharp JT, Wilson P, Parsons S, Gould RO (2000) J Chem Soc Perkin Trans 1:1139
Dömling A (2006) Chem Rev 106:17
Zhu J, Bienayme H (2005) Multicomponent reactions. Wiley-VCH, Weinheim
Maisonneuve S, Xie J (2009) Synlett 20(18):2977
Reddy Udagandla C, Saikia Anil K (2010) Synlett 21(7):1027
Ranjabar-Karimi R, Beiki-Shoraki K, Amiri A (2010) Monatsh Chem 141:1101
Keri RS, Hosamani KM (2010) Monatsh Chem 141:883
Gladkov ES, Sirko SN, Shishkina SV, Shishkin OV, Knyazeva IV, Desenko SM, Chebanov VA (2010) Monatsh Chem 141:773
Wang HJ, Zhang XN, Zhang ZH (2010) Monatsh Chem 141:425
Yavari I, Sayyed-Alangy SZ, Hajinasiri R, Sajjadi-Ghotbabadi H (2009) Monatsh Chem 140:209
Dumitrascu F, Draghici C, Caproiu MT, Dumitrescu DG, Popa MM (2009) Rev Roum Chim 53:923
Georgescu E, Caira MR, Georgescu F, Draghici B, Popa MM, Dumitrascu F (2009) Synlett 20(11):1795
Caira MR, Georgescu E, Georgescu F, Draghici B, Popa MM, Dumitrascu F (2009) Arkivoc xii:242
Dumitrascu F, Caproiu MT, Georgescu F, Draghici B, Popa MM, Georgescu E (2010) Synlett 21(16):2407
Dumitrascu F, Georgescu E, Caira MR, Georgescu F, Popa MM, Draghici B, Dumitrescu DG (2009) Synlett 20(20):3336
Georgescu E, Dumitrascu F, Georgescu F, Draghici C, Popa MM (2010) Rev Roum Chim 55:217
Hooft R (1988) V. Collect: Data Collection Software, Nonius BV, Delft, The Netherlands
Otwinowski Z, Minor W (1997) Methods Enzymol 276:307
Sheldrick GM (2008) Acta Cryst A64:112
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M.R.C. thanks the University of Cape Town and the National Research Foundation for research support.
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Caira, M.R., Georgescu, E., Georgescu, F. et al. Contributions to syntheses of pyrrolo[2,1-a]phthalazines. Monatsh Chem 142, 743–748 (2011). https://doi.org/10.1007/s00706-011-0468-8
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DOI: https://doi.org/10.1007/s00706-011-0468-8