Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(02): 564-572
DOI: 10.1055/s-0037-1609940
DOI: 10.1055/s-0037-1609940
paper
Synthesis of Aryl-Substituted 3,3a,4,5-Tetrahydropyrrolo[1,2-a] quinolin-1(2H)-ones and 2,3,4,4a,5,6-Hexahydro-1H-pyrido[1,2-a]quinolin-1-ones
F.M.W. wishes to acknowledge the NSF for REU funding (CHE-1559874) during the summer of 2017 and the Wentz Foundation for an Undergraduate Research Scholarship during the 2017–2018 academic year. The authors are also grateful for support from the NSF (BIR-9512269), the Oklahoma State Regents for Higher Education, the W. M. Keck Foundation, and Conoco, Inc. that established the Oklahoma State-wide NMR facility. The authors also thank the Oklahoma State University College of Arts and Sciences for funds that allowed the Chemistry Department to purchase a new 400 MHz NMR for this facility.Further Information
Publication History
Received: 10 June 2018
Accepted after revision: 07 August 2018
Publication Date:
05 September 2018 (online)
Abstract
A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- and 2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure affords the final lactam products. The reactions proceed cleanly and only two chromatographic purifications are required.
Key words
benzo-fused lactams - alkylation–decarboxylation - β-keto diesters - reductive amination - ester hydrolysis - lactamizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609940.
- Supporting Information
-
References
- 1a Michael JP. Nat. Prod. Rep. 2007; 24: 191
- 1b Yao Z. Wei X. Wu X. Katz JL. Kopajtic T. Grieg NH. Eur. J. Med. Chem. 2011; 46: 1841
- 1c Bernardim B. Lordello LD. Burtoloso AC. B. Curr. Top. Med. Chem. 2013; 13: 2099
- 1d Brambilla M. Davies SG. Fletcher AM. Roberts PM. Thomson JE. Tetrahedron 2014; 70: 204
- 1e Davies SG. Fletcher AM. Foster EM. Houlsby IT. T. Roberts PM. Schofield TM. Thomson JE. Org. Biomol. Chem. 2014; 12: 9223
- 1f Brambilla M. Davies SG. Fletcher AM. Roberts PM. Thomson JE. Zimmer D. Tetrahedron 2016; 72: 7417
- 1g Brambilla M. Davies SG. Fletcher AM. Roberts PM. Thomson JE. Tetrahedron 2016; 72: 7449
- 2a Szmuszkovicz J. Regan C. WO2000004905A1, 2000 ; Chem. Abstr. 2000, 132, 122528
- 2b Szczesniak P. Ulikowski A. Staszewska-Krajewska O. Lipner G. Furman B. Tetrahedron 2016; 72: 3032
- 3 Meyers AI. Milot G. J. Org. Chem. 1993; 58: 6538
- 4 Wolfe JP. Rennels RA. Buchwald SL. Tetrahedron 1996; 52: 7525
- 5 Lee J. Ha JD. Cha JK. J. Am. Chem. Soc. 1997; 119: 8127
- 6 Pearson WH. Fang W. J. Org. Chem. 2000; 65: 7158
- 7 Shirai A. Miyata O. Tohnai N. Miyata M. Procter DJ. Sucunza D. Naito T. J. Org. Chem. 2008; 73: 4464
- 8 Baumgarten HE. Beckerbauer R. DeBrunner MR. J. Org. Chem. 1961; 26: 1539
- 9 Lompa-Krzymien L. Leitch LC. Pol. J. Chem. 1978; 52: 107
- 10 Akiba M. Ohki S. Yakugaku Zasshi 1970; 90: 1193 ; Chem. Abstr. 1971, 74, 12977
- 11 Kocian O. Ferles M. Collect. Czech. Chem. Commun. 1978; 43: 1413
- 12 Song L. Liu K. Li C. Org. Lett. 2011; 13: 3434
- 13 Ye L. Lo K.-Y. Gu Q. Yang D. Org. Lett. 2017; 19: 308
- 14 Tsoung J. Wang Y. Djuric SW. React. Chem. Eng. 2017; 2: 458
- 15 Davidson D. Bernhard SA. J. Am. Chem. Soc. 1948; 70: 3426
- 16 Oikawa Y. Sugano K. Yonemitsu O. J. Org. Chem. 1978; 43: 2087
- 17 Oikawa Y. Yoshioka T. Sugano K. Yonemitsu O. Org. Synth. Coll. Vol. VII 1990; 359-361
- 18 Bunce RA. Nago T. Sonobe N. Slaughter LM. J. Heterocycl. Chem. 2008; 45: 551
- 19 Borowiecki L. Kazubski A. Pol. J. Chem. 1978; 52: 1447
- 20 Bunce RA. Nago T. J. Heterocycl. Chem. 2008; 45: 1155
- 21 Bunce RA. Nammalwar B. J. Heterocycl. Chem. 2009; 46: 172
- 22 McLaughlin M. Belyk K. Chen C. Linghu X. Pan J. Qian G. Reamer RA. Xu Y. Org. Proc. Res. Dev. 2013; 17: 1052
- 23 Al Othman ZA. Apblett AW. Appl. Surf. Sci. 2010; 256: 3573
- 24 Nammalwar B. Muddala NP. Watts FM. Bunce RA. Tetrahedron 2015; 71: 9101
- 25 Singh B. Tetrahedron Lett. 1971; 321
Review:
Recent work:
Benzo-fused derivatives: