Synthesis, Table of Contents Synthesis 2023; 55(03): 465-472DOI: 10.1055/a-1932-5811 paper New Efficient Synthesis of 6,12-Dihydro-5H-quinazolino[3,2-a] quinazolin-5-ones via Ugi/Staudinger/Aza-Wittig/Addition/Nucleophilic Acyl Substitution Sequence Mao-Lin Yang , Hao-Ran Chen , Long Zhao , Ming-Wu Ding ∗Recommend Article Abstract Buy Article All articles of this category Abstract A new efficient synthesis of 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones by sequential Ugi/Staudinger/aza-Wittig/addition/nucleophilic acyl substitution has been developed. α-Amino amides, obtained from Ugi-3CR of 2-azidobenzaldehydes, methyl 2-aminobenzoates, and isocyanides in the presence of catalytic amount of phenylphosphinic acid, reacted with triphenylphosphine and isocyanates to give 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones in good yields. This method provides a domino and effective strategy for the preparation of various substituted quinazolino[3,2-a]quinazolin-5-ones under mild reaction condition. Key words Key wordsquinazoline - 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-one - Ugi reaction - Staudinger reaction - aza-Wittig reaction Full Text References References 1a Ozaki KI, Yamada Y, Oine T. Chem. Pharm. Bull. 1984; 32: 2160 1b Ahmed Kamal A, Sattur PB. Arch. Pharm. (Weinheim) 1983; 316: 702 2 Zhang J, Liu J, Ma YM, Ren DC, Cheng P, Zhao JW, Zhang F, Yao Y. Bioorg. Med. Chem. Lett. 2016; 26: 2273 3 Aly MM, Mohamed YA, El-Bayouki KA, Basyouni WM, Abbas SY. Eur. J. Med. Chem. 2010; 45: 3365 4 Bouley R, Ding D, Peng ZH, Bastian M, Lastochkin E, Song W, Suckow MA, Schroeder VA, Wolter WR, Mobashery S, Chang M. J. Med. Chem. 2016; 59: 5011 5a Mohamed MA, Ayyad RR, Shawer TZ, Abdel-Aziz AA. M, El-Azab AS. Eur. J. Med. Chem. 2016; 112: 106 5b Huang W.-Y, Zhang X.-R, Lyu L, Wang S.-Q, Zhang X.-T. Bioorg. Chem. 2020; 99: 103814 6 Chiou W.-F, Liao J.-F, Chen C.-F. J. Nat. Prod. 1996; 59: 374 7 Yang S, Li X, Hu F, Li Y, Yang Y, Yan J, Kuang C, Yang Q. J. Med. Chem. 2013; 56: 8321 8 Cagir A, Jones SH, Gao R, Eisenhauer BM, Hecht SM. J. Am. Chem. Soc. 2003; 125: 13628 9 Banerji B, Bera S, Chatterjee S, Killi SK, Adhikary S. Chem. Eur. J. 2016; 22: 3506 10 Zeng F, Alper H. Org. Lett. 2010; 12: 3642 11 Grover RK, Kesarwani AP, Srivastava GK, Kundu B, Roya R. Tetrahedron 2005; 61: 5011 12 Guo S, Zhai J, Fan X. Org. Biomol. Chem. 2017; 15: 1521 13 Hao W, Li K, Ye C, Yu W, Chang J. Org. Lett. 2022; 24: 3286 14 Ly D, Nguyen TT, Tran CT. H, Nguyen VP. T, Nguyen KX, Pham PH, Le NT. H, Nguyen TT, Phan NT. S. J. Org. Chem. 2022; 87: 103 15 Zhang J, Wang X, Chen D, Kang Y, Ma Y, Szostak M. J. Org. Chem. 2020; 85: 3192 16 Ren ZL, Kong HH, Lu WT, Sun M, Ding MW. Tetrahedron 2018; 74: 184 17a Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083 17b Rotstein BH, Zaretsky S, Rai V, Yudin AK. Chem. Rev. 2014; 114: 8323 17c Manar Ahmed Fouad MA, Abdel-Hamid H, Ayoup MS. RSC Adv. 2020; 10: 42644 18a Pan CS, List B. Angew. Chem. Int. Ed. 2008; 47: 3622 18b Kumar A, Saxena D, Gupta MK. Green Chem. 2013; 15: 2699 18c Khan AT, Basha RS, Lal M, Mir MH. RSC Adv. 2012; 2: 5506 18d Guan ZR, Wan Q, Ding MW. Tetrahedron 2019; 75: 4626 18e Schofield K, Foley C, Hulme C. Org. Lett. 2021; 23: 107 19a Tripolitsiotis NP, Thomaidi M, Neochoritis CG. Eur. J. Org. Chem. 2020; 6525 19b Flores-Reyes JC, Islas-Jácome A, González-Zamora E. Org. Chem. Front. 2021; 8: 5460 20 Nechaev AA, Van Hecke K, Zaman M, Kashtanov S, Ungur L, Pereshivko OP, Peshkov VA, Van der Eycken EV. J. Org. Chem. 2018; 83: 8170 21 Schofield K, Foley C, Hulme C. Org. Lett. 2021; 23: 107 22 Lei J, Song G.-T, Luo Y.-F, Tang D.-Y, Yan W, Li HY, Chen ZZ, Xu Z.-G. Org. Chem. Front. 2020; 7: 737 23 Wang Y, Patil P, Kurpiewska K, Kalinowska-Tluscik J, Dömling A. Org. Lett. 2019; 21: 3533 24 Zhang B, Kurpiewska K, Dömling A. J. Org. Chem. 2022; 87: 7085 25 Borja-Miranda A, Sánchez-Chávez AC, Polindara-García LA. Eur. J. Org. Chem. 2019; 2453 26 Bhela IP, Serafini M, Grosso ED, Tron GC, Pirali T. Org. Lett. 2021; 23: 3610 27 Mazur MO, Zhelavskyi OS, Zviagin EM, Shishkina SV, Musatov VI, Kolosov MA, Shvets EH, Andryushchenko AY, Chebanov VA. Beilstein J. Org. Chem. 2021; 17: 678 28 Amador-Sánchez YA, Hernández-Vázquez E, González-Mojica N, Ramírez-Apan MT, Miranda LD. Tetrahedron 2020; 76: 131383 29 Pedrood K, Montazer MN, Larijani B, Mahdavi M. Synthesis 2021; 53: 2342 30a Polychronidou V, Krupp A, Strohmann C, Antonchick AP. Org. Lett. 2021; 23: 6024 30b Ma X, Zhang X, Awad JM, Xie G, Qiu W, Muriph RE, Zhang W. Tetrahedron Lett. 2020; 61: 151392 30c Zhang X, Ma X, Qiu W, Awad JM, Evans J, Zhang W. Adv. Synth. Catal. 2020; 362: 5513 30d Alaime T, Daniel M, Hiebel M.-A, Pasquinet E, Suzenet F, Guillaumet G. Chem. Commun. 2018; 54: 8411 30e Dagar A, Kim I. Org. Biomol. Chem. 2020; 18: 9836 30f Zou F, Pei F, Wang L, Ren Z, Cheng X, Sun Y, Wu J, He P. Synlett 2019; 30: 717 31a Wu J, Zhao L, Yang ML, Ding MW. J. Org. Chem. 2021; 86: 10755 31b Zhao L, Yang ML, Liu M, Ding MW. Beilstein J. Org. Chem. 2022; 18; 286 31c Sun M, Zhao L, Yu YL, Ding MW. Synthesis 2021; 53: 1365 31d Sun M, Yu YL, Zhao L, Ding MW. Tetrahedron 2021; 77: 131868 31e Sun M, Zhao L, Ding MW. J. Org. Chem. 2019; 84: 14313 Supplementary Material Supplementary Material Supporting Information
