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Synthesis 2022; 54(16): 3623-3630
DOI: 10.1055/a-1828-1560
DOI: 10.1055/a-1828-1560
paper
A Strategy for the Synthesis of Bicyclic Fused Cyclopentenones from MBH-Carbonates of Propiolaldehydes
C.R.R. thanks the Science and Engineering Research Board (SERB), New Delhi, for funding the project (EMR/2016/006253). Authors thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for research fellowships. [CSIR-IICT Communication No. IICT/Pubs./2022/013].
Abstract
An effective synthetic approach has been demonstrated for the construction of diverse bicyclic fused cyclopentenones from Morita–Baylis–Hillman (MBH) carbonates of propiolaldehydes. The present transformation was initiated through the propargylation of an alkenylamine with an MBH carbonate followed by the Pauson–Khand reaction of the product methyl 3-(alkenylamino)-2-methylenealk-4-ynoate. This facile method provides diverse scaffolds of cyclopentenone fused with aza-cycles having additional functionality in good yields.
Keywords
nitrogen heterocycles - cyclopentenones - propargylation - Pauson–Khand reaction - Morita–Baylis–Hillman (MBH) adductSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1828-1560.
- Supporting Information
Publication History
Received: 13 January 2022
Accepted after revision: 19 April 2022
Accepted Manuscript online:
19 April 2022
Article published online:
30 May 2022
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References
- 1a Imanishi T, Yagi N, Hanaoka M. Tetrahedron Lett. 1981; 22: 667
- 1b Imanishi T, Yagi N, Hanaoka M. Chem. Pharm. Bull. 1983; 31: 1243
- 1c Alazaed JP, Leboff A, Thal C. Tetrahedron Lett. 1989; 30: 5267
- 1d Puder C, Krastel P, Zeeck A. J. Nat. Prod. 2000; 63: 1258
- 1e Kavanagh Y, O’Brien M, Evans P. Tetrahedron 2009; 65: 8259
- 1f Kam T.-S, Yoganathan K, Wei C. J. Nat. Prod. 1997; 60: 673
- 1g Lozoya-Meckes M, Mellado-Campos V. J. Ethnopharmacol. 1985; 14: 1
- 2a Yoo S, Lee SH. J. Org. Chem. 1994; 59: 6968
- 2b Kaneda K, Honda T. Tetrahedron 2008; 64: 11589
- 2c Clark JS, Xu C. Angew. Chem. Int. Ed. 2016; 55: 4332
- 3a Pansare SV, Lingampally R. Org. Biomol. Chem. 2009; 7: 319
- 3b Fall Y, Doucet H, Santelli M. Tetrahedron 2009; 65: 489
- 3c Kwok S, Hein WJ. E, Fokin VV, Sharpless KB. Heterocycles 2008; 76: 1141
- 3d Acharya HP, Miyoshi K, Takashima Y, Ogawa N, Kobayashi Y. Heterocycles 2008; 76: 1181
- 3e Takasu K, Inanaga K, Ihara M. Tetrahedron Lett. 2008; 49: 4220
- 3f Gomes RF. A, Coelho JA. S, Afonso CA. M. ChemSusChem 2019; 12: 420
- 4a Duran-Lara EF, Shankaraiah N, Geraldo D, Santos LS. J. Braz. Chem. Soc. 2009; 20: 813
- 4b Tang Y, Deng L, Zhang Y, Dong G, Chen J, Yang Z. Org. Lett. 2005; 7: 1657
- 4c Shibata T, Toshida N, Takagi K. J. Org. Chem. 2002; 68: 7446
- 4d Cochrane AR, Kerr WJ, Paterson LC, Pearson CM, Shaw P. Tetrahedron 2021; 78: 131805
- 4e Nag S, Batra S. Tetrahedron 2011; 67: 8959
- 4f Comely AC, Gibson SE, Stevenazzi A, Hales NJ. Tetrahedron Lett. 2001; 42: 1183
- 4g Kim S.-W, Son SU, Lee SS, Hyeon T, Chung YK. Chem. Commun. 2001; 2212
- 4h Lee HW, Lee LN, Chan AS. C, Kwong FY. Eur. J. Org. Chem. 2008; 3403
- 4i Krafft ME, Bonaga LV. R, Hirosawa C. J. Org. Chem. 2001; 66: 3004
- 4j Shibata T, Toshida N, Takagi K. Org. Lett. 2002; 4: 1619
- 4k Kaur N, Ahlawat N, Verma Y, Bhardwaj P, Grewal P, Jangid NK. Inorg. Nano-Met.Chem. 2020; 12: 1260
- 4l Reddy CR, Reddy MD, Srikanth B. Org. Biomol. Chem. 2012; 10: 4280
- 4m Gibson SE, Johnstone C, Stevenazzi A. Tetrahedron 2002; 58: 4937
- 4n Sturla SJ, Buchwald SL. J. Org. Chem. 1999; 64: 5547
- 5a Nazarov IN, Zaretskaya II. Bull. Acad. Sci. URSS 1942; 200
- 5b Habermas KL, Denmark SE, Jones TK. Org. React. 1994; 45: 1
- 5c Tius MA. Eur. J. Org. Chem. 2005; 2193
- 5d Pellissier H. Tetrahedron 2005; 61: 6479
- 5e Frontier AJ, Collison C. Tetrahedron 2005; 61: 7577
- 5f Vinogradov MG, Turova OV, Zlotin SG. Org. Biomol. Chem. 2017; 15: 8245
- 6a Gibson SE, Lewis SE, Mainolfi N. J. Organomet. Chem. 2004; 689: 3873
- 6b Cleary SE, Hensinger MJ, Brewer M. Chem. Sci. 2017; 8: 6810
- 6c Reddy CR, Kumaraswamy P, Singarapu KK. J. Org. Chem. 2014; 79: 7880
- 7 Yadykov AV, Shirinian VZ. Adv. Synth. Catal. 2020; 362: 702
- 8a Khand IU, Knox GR, Pauson PL, Watts WE. J. Chem. Soc. 1971; 36
- 8b Keun Chung Y. Coord. Chem. Rev. 1999; 188: 297
- 8c Gibson SE, Stevenazzi A. Angew. Chem. Int. Ed. 2003; 42: 1800
- 8d Wasilke J.-C, Obrey SJ, Baker RT, Bazan GC. Chem. Rev. 2005; 105: 1001
- 9a Ockey DA, Lewis MA, Schore NE. Tetrahedron 2003; 59: 5377
- 9b Lee H.-W, Kwong F.-Y. Eur. J. Org. Chem. 2010; 789
- 9c Brummonda KM, Kent JL. Tetrahedron 2000; 56: 3263
- 9d Yang Z. Acc. Chem. Res. 2021; 54: 556
- 9e Chen S, Jiang C, Zheng N, Yang Z, Shi L. Catalysts 2020; 10: 1199
- 10a Reddy CR, Patil AD. Org. Lett. 2021; 23: 4749
- 10b Reddy CR, Patil AD, Mohammed SZ. Chem. Commun. 2020; 56: 7191
- 10c Reddy CR, Mohammed SZ, Kumaraswamy P. Org. Biomol. Chem. 2015; 13: 8310
- 10d Reddy CR, Reddy MD, Srikanth B, Prasad KR. Org. Biomol. Chem. 2011; 9: 6027
- 11 Vakulya B, Varga S, Csámpai A, Soós T. Org. Lett. 2005; 7: 1967
- 12a Mukai C, Kim JS, Sonobe H, Hanaoka M. J. Org. Chem. 1999; 64: 6822
- 12b Cassayre J, Gagosz F, Zard SZ. Angew. Chem. Int. Ed. 2002; 41: 1783
- 13 Jacquet O, Bergholz T, Magnier-Bouvier C, Mellah M, Guillot R, Flaud J.-C. Tetrahedron 2010; 66: 222
For representative references, see: