Synthesis of heterocyclic compounds using ring-closing enyne metathesis reaction

Titas Biswas

doi:10.52756/ijerr.2020.v22.003

Authors

Titas Biswas Department of Chemistry, Gurudas College, Kolkata 700054, West Bengal, India

DOI:

https://doi.org/10.52756/ijerr.2020.v22.003

Keywords:

Enyne metathesis, Diels Alder reaction, aromatisation

Abstract

Ring-closing enyne metathesis reaction has emerged as an elegant tool in organic synthesis for the creation of molecular complexity and used to prepare diverse heterocycles. In this mini review, I discuss that various linearly and angularly architecture heterocyclic compounds may be prepared using RCEM as key steps.

References

Barrett, A. G. M., Ahmed, M., Baker, S. P., Baugh, S. P. D., Braddock, D. C., Procopiou, P. A., White, A. J. P. and Williams, D. J. (2000). Tandem Ireland− Claisen Rearrangement Ring-Closing Alkene Metathesis in the Construction of Bicyclic β-Lactam Carboxylic Esters. J. Org. Chem. 65 (12): 3716-3721.

Biswas, T., Biswas, T. and Chattopadhyay, S. K. (2010). Synthesis of chiral oxa- and azacycle-fused anthraquinone derivatives. Tetrahedron Asymmetry. 21: 232-236.

Chattopadhyay, S. K., Biswas, T. and Neogi, K. (2006). Synthesis of Polycyclic Coumarin Derivatives by Combined Claisen Rearrangement, Ring-closing Metathesis, and Diels–Alder Reaction. Chem. Lett. 35: 376-377.

Chattopadhyay, S. K., Karmakar, S., Biswas, T., Majumder, K. C., Rahaman, H. and Roy, B. (2007). Formation of medium-ring heterocycles by diene and enyne metathesis. Tetrahedron. 36: 3919- 3952.

Chattopadhyay, S. K., Roy, S. P., Ghosh, D. and Biswas, G. (2006). Synthesis of oxepine- , oxocine-and azepine-annulated carbazole derivatives by combined Claisen rearrangement and diene/enyne metathesis. Tetrahedron Lett. 47: 6895-6898.

Clark, J. S., Elustondo, F., Trevitt, G. P., Boyall, D., Robertson, J., Blake, A. J., Wilson, C. and Stammen, B. (2002). Preparation of cyclic ethers for polyether synthesis by catalytic ring-closing enyne metathesis of alkynyl ethers. Tetrahedron. 58: 1973-1982.

Diver, S. T. and Giessert, A. (2004). Enyne Metathesis (Enyne Bond Reorganization). J. Chem. Rev. 104: 1317-1382.

Fürstner, A., Ackermann, L., Gabor, B., Goddard, R., Lehmann, C. W., Mynott, R., Stelzer, F. and Thiel, O. R. (2001). Comparative Investigation of Ruthenium-Based Metathesis Catalysts Bearing N-Heterocyclic Carbene (NHC) Ligands. Chem. Eur. J. 7: 3236-3253.

Hoye, R. T., Donaldson, S. M. and Vos, T. (1999).An Enyne Metathesis/ (4 + 2)- Dimerization Route to (±)-Differolide. Org. Lett. 1: 277-279.

Kinoshita, A. and Mori, M. (1996). Total synthesis of (−)-stemoamide using ruthenium-catalyzed enyne metathesis reaction. J. Org. Chem. 61: 8356- 8357.

Kinoshita, A. and Mori, M. (1997). Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction. Heterocycles. 46: 287-299.

Kotha, S., Chavan, A. S. and Goyal, D. (2019). Diversity-Oriented Approaches to Polycycles and Heterocycles via Enyne Metathesis and Diels−Alder Reaction as Key Steps. ACS Omega. 4: 22261-22273.

Kotha, S. and Sreenivasachary, N. (2000). A new synthetic approach to 1, 2, 3, 4- tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives via enyne metathesis and the Diels–Alder reaction. Chem. Commun. 12 (6): 503- 504.

Litvinov, V. P., Roman, S. V. and Dyachenko, V. D. (2000). Naphthyridines. Structure, physicochemical properties and general methods of synthesis. Russ. Chem. Rev. 69: 201-220.

Majumdar, K. C., Rahaman, H., Muhuri, S. and Roy, B. (2006). Stereo-selective synthesis of tricyclic pyranoxepin derivatives by ruthenium-catalyzed enyne metathesis/Diels-Alder reaction. Synlett. 2006 (3): 466-468.

Majumdar, K. C., Rahaman, H., Islam, B. and Roy, B. (2006). Tandem Claisen rearrangement and ruthenium catalyzed enyne bond reorganization as a route to the synthesis of tricyclic 1, 8- naphthyridinones. Tetrahedron Lett. 47 (27): 2111-2113.

Moreno-Manas, M., Pleixats, R. and Santamaria, A. (2001). Preparation of tricyclic and tetracyclic benzoxepin derivatives by one-pot enyne metathesis/Diels-Alder reaction. Synlett. 2001 (11): 1784-1786.

Mori, M. (1998). Alkene Metathesis in Organic Synthesis. Top. Organomet. Chem. 1: 133-154.

Mori, M., Kitamura, T., Sakakibara, N. and Sato, Y. (2000). Synthesis of eightmembered ring compounds using enyne metathesis. Org. Lett. 2: 543- 545.

Mori, M., Kitamura, T. and Sato, Y. (2001). Synthesis of Medium-Sized Ring Compounds Using Enyne Metathesis. Synthesis. 4: 654-664.

Mori, M., Sakakibara, N. and Kinoshita, A. (1998). Remarkable Effect of Ethylene Gas in the Intra-molecular Enyne Metathesis of Terminal Alkynes. J. Org. Chem. 63: 6082-6083.

Murakami, A., Gao, G., Omura, M., Yano, M., Ito, C., Furukawa, H., Takahasi, D., Koshimizu, K. and Ohigashi, H. B. M. (2000). 1, 1-Dimethylallylcoumarins potently suppress both lipopolysaccharide-and interferon-γinduced nitric oxide generation in mouse macrophage RAW 264.7 cells. Chem. Lett. 10: 59.

Poulsen, C. S. and Madsen, R. (2003). Enyne metathesis catalyzed by ruthenium carbene complexes. Synthesis. 1: 1-18.

Renaud, J., Graf, C. D. and Oberer, L. (2000).Ruthenium-Catalyzed Enyne Metathesis of Acetylenic Boronates: A Concise Route for the Construction of Cyclic 1, 3-Dienylboronic Esters. Angew. Chem. Int. Ed. 39: 3101-3104.

Sayyad, A. A. and Kaliappan, K. P. (2017). Sequential Enyne-Metathesis/DielsAlder Strategy: Rapid Accessto the Novel Sugar-oxasteroid-quinone Hybrids. Eur. J. Org. Chem. 34: 5055- 5065.

Schramm, M. P., Reddy, D. S. and Kozmin, S. A. (2001). Siloxyalkyne–Alkene Metathesis: Rapid Access to Highly Functionalized Enones. Angew. Chem. Int. Ed. 40: 4274-4277.

Wu, J., Liao, Y. and Yang, Z. (2001). Synthesis of 4-substituted coumarins via the palladium-catalyzed cross-couplings of 4-tosylcoumarins with terminal acetylenes and organo-zinc reagents. J. Org. Chem. 66 (10): 3642-3645.