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DOI: 10.1055/a-1534-0466
Elemental Sulfur Mediated Synthesis of Pyrrolo[1,2-a]quinoxalines from 1-(2-Nitroaryl)pyrroles
Authors
We thank the Viet Nam National University Ho Chi Minh City (VNU-HCM) for financial support via project no. NCM2019-20-01 (for N.T.S.P.).
Abstract
Methods to afford pyrrolo[1,2-a]quinoxalines often require the use of prefunctionalized aniline precursors, transition metals, and/or harsh conditions. Herein we describe a simple coupling of 1-(2-nitroaryl)pyrroles and arylacetic acids, in the presence of elemental sulfur, to furnish the fused heterocycles in good yields. The conditions are compatible with many functionalities including ester, nitrile, halogen, and nitro groups. Use of benzyl alcohols and picoline coupling reagents was also attempted.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1534-0466.
- Supporting Information (PDF)
Publication History
Received: 21 May 2021
Accepted after revision: 22 June 2021
Accepted Manuscript online:
22 June 2021
Article published online:
22 July 2021
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References
- 1a Muto K, Okita T, Yamaguchi J. ACS Catal. 2020; 10: 9856
- 1b Gao Y, Yang S, Huo Y, Hu X.-Q. Adv. Synth. Catal. 2020; 362: 3971
- 2a Pereira M. dF, Thiéry V. Org. Lett. 2012; 14: 4754
- 2b Chun S, Ahn J, Putta RR, Lee SB, Oh D.-C, Hong S. J. Org. Chem. 2020; 85: 15314
- 2c Rubio-Presa R, Pedrosa MR, Fernández-Rodríguez MA, Arnáiz FJ, Sanz R. Org. Lett. 2017; 19: 5470
- 2d Sun Q, Liu L, Yang Y, Zha Z, Wang Z. Chin. Chem. Lett. 2019; 30: 1379
- 2e To TA, Nguyen CT, Tran MH. P, Huynh TQ, Nguyen TT, Le NT. H, Nguyen AD, Tran PD, Phan NT. S. J. Catal. 2019; 377: 163
- 3a Wang T, Tang Y, Yang Y, An Q, Sang Z, Yang T, Liu P, Zhang T, Deng Y, Luo Y. Bioorg. Med. Chem. Lett. 2018; 28: 2084
- 3b Alleca S, Corona P, Loriga M, Paglietti G, Loddo R, Mascia V, Busonera B, La Colla P. Farmaco 2003; 58: 639
- 3c Çarbaş BB, Kivrak A, Zora M, Önal AM. React. Funct. Polym. 2011; 71: 579
- 4a Nguyen TB. Adv. Synth. Catal. 2020; 362: 3448
- 4b Liu S, Deng G.-J, Huang H. Synlett 2021; 32: 142
- 5a Dang M.-HD, Nguyen LH. T, Tran PH. Synthesis 2020; 52: 1687
- 5b Nguyen KX, Nguyen DK, Pham PH, Le HV, Nguyen TT, Phan NT. S. Synlett 2020; 31: 1112
- 6a Nguyen TB, Ermolenko L, Corbin M, Al-Mourabit A. Org. Chem. Front. 2014; 1: 1157
- 6b Guntreddi T, Vanjari R, Singh KN. Org. Lett. 2015; 17: 976
- 6c Do NT, Tran KM, Phan HT, To TA, Nguyen TT, Phan NT. S. Org. Biomol. Chem. 2019; 17: 8987
- 7 Pentsak EO, Eremin DB, Gordeev EG, Ananikov VP. ACS Catal. 2019; 9: 3070
- 8a Nguyen TB, Retailleau P. Org. Lett. 2019; 21: 279
- 8b Nguyen TB, Ermolenko L, Al-Mourabit A. Org. Lett. 2012; 14: 4274
- 9 Jiang G, Wang S, Zhang J, Yu J, Zhang Z, Ji F. Adv. Synth. Catal. 2019; 361: 1798
- 10 Lade JJ, Patil BN, Vhatkar MV, Vadagaonkar KS, Chaskar AC. Asian J. Org. Chem. 2017; 6: 1579
- 11 Lv W, Budke B, Pawlowski M, Connell PP, Kozikowski AP. J. Med. Chem. 2016; 59: 4511
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