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Synthesis 2017; 49(01): 135-144
DOI: 10.1055/s-0035-1562792
DOI: 10.1055/s-0035-1562792
paper
On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones
Further Information
Publication History
Received: 15 June 2016
Accepted after revision: 08 July 2016
Publication Date:
24 August 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201701/lookinside/thumbnails/ss-2016-z0435-op_10-1055_s-0035-1562792-1.jpg)
Dedicated with respect and best wishes to our friend Dieter Enders on the occasion of his 70th birthday
Abstract
An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported.
Key words
quinazolinone - alkaloid - 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one - deoxyvasicinoneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562792.
- Supporting Information
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References
- 1 Department of Chemistry, Imperial College, London, SW7 2AZ.
- 2 Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 3 Connolly DJ, Cusack D, Sullivan TP. O, Guiry PJ. Tetrahedron 2005; 61: 10153
- 4 Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
- 5 Johns S, Lamberton JA. J. Chem. Soc., Chem. Commun. 1965; 267
- 6 Fitzgerald JS, Johns SR, Lamberton JA, Redcliffe AH. Aust. J. Chem. 1966; 19: 151
- 7 Cho J, Bae S, Kim H, Lee M, Choi Y, Jin B, Lee HJ, Jeong HY, Lee YG, Moon J. J. Agric. Food Chem. 2015; 63: 3587
- 8 Moehrle H, Hemmerling HJ. Arch. Pharm. (Weinheim) 1978; 311: 586
- 9 Hassanzadeh F, Jafari E, Hakimelahi GH, Rahmani Khajouei M, Jalali M, Khodarahmi GA. Res Pharm Sci 2012; 7: 87
- 10 Sutherell CL, Tallant C, Monteiro OP, Yapp C, Fuchs JE, Fedorov O, Siejka P, Müller S, Knapp S, Brenton JD, Brennan PE, Ley SV. J. Med. Chem. 2016; 57: 5095
- 11 Nazarenko KG, Shyrokaya TI, Tolmachev AA. Synth. Commun. 2008; 33: 303
- 12 Dunn AD, Kinnear KI. J. Heterocycl. Chem. 1986; 23: 53
- 13 Sun X, Hu Y, Nie S, Yan Y, Zhang X. Adv. Synth. Catal. 2013; 355: 2179
- 14 Jones AM, Lebl T, Patterson S, van Mourik T, Früchtl HA, Philp D, Slawin AM. Z, Westwood NJ. Tetrahedron 2009; 65: 563
- 15 Zhu Y, Fei Z, Liu M, Jia F, Wu A. Org. Lett. 2013; 15: 378
- 16 Moorthy JN, Senapati K, Parida KN, Jhulki S, Sooraj K, Nair NN. J. Org. Chem. 2011; 76: 9593
- 17 Cheng X, Vellalath S, Goddard R, List B. J. Am. Chem. Soc. 2008; 130: 15786
- 18 Tu T, Wang Z, Liu Z, Feng X, Wang Q. Green Chem. 2012; 14: 921
- 19 Möhrle H, Seidel C.-M. Arch. Pharm. (Weinheim) 1976; 309: 542
- 20 Elmuradov BZ, Abdurazakov AS, Shakhidoyatov KM. Chem. Nat. Compd. 2008; 44: 475
- 21 Il’chenko AY, Nazarenko KG, Shirokaya TI, Tolmachev AA, Tolmachev AI. Ukr. Khim. Zh. 2003; 69: 48
- 22 Bubenyák M, Pálfi M, Takács M, Béni S, Szökó E, Noszál B, Kökösi J. Tetrahedron Lett. 2008; 49: 4937
- 23 Voitenko ZV, Halaev OI, Samoylenko VP, Kolotilov SV, Lepetit C, Donnadieu B, Chauvin R. Tetrahedron 2010; 66: 8214
- 24 Primary data related to this publication (NMR files, processed NMR spectra, IR files, IR pdf files) are available at http://dx.doi.org/10.17863/CAM.523.
- 25 Darras FH, Kling B, Heilmann J, Decker M. ACS Med. Chem. Lett. 2012; 3: 914
- 26 Yan JW, Li YP, Ye WJ, Chen SB, Hou JQ, Tan JH, Ou TM, Li D, Gu LQ, Huang ZS. Bioorg. Med. Chem. 2012; 20: 2527