Transition-Metal-Free Heterocyclization of 1,3-Diynes with Nitriles in the Presence of Aqueous Potassium Hydroxide: Synthesis of 2,4-Disubstituted 5-[(E)-2-Phenylethenyl]-1,3-oxazoles

Abstract

A transition-metal-free heterocyclization of 1,3-diynes and nitriles in the presence of either aqueous potassium hydroxide or cesium hydroxide in 1,4-dioxane at 100 °C was realized. This method provided stereoselectively 2,4-disubstituted 5-[(E)-2-phenylethenyl]-1,3-oxazoles in moderate to good yields.

Key words

1,3-diyne - nitrile - heterocyclization - cesium hydroxide - potassium hydroxide

• References

• 1a Atkins JM, Vedejs E. Org. Lett. 2005; 7: 3351
• 1b Zhang J, Ciufolini MA. Org. Lett. 2009; 11: 2389
• 1c Vedejs E, Barda DA. Org. Lett. 2000; 2: 1033
• 1d Walsh CT, Macolmson SJ, Young TS. Chem. Bio. 2012; 7: 429
• 2a Desroy N, Moreau F, Briet S, Le Fralliec G, Floquet S, Durant L, Vongsouthi V, Gerusz V, Denis A, Escaich S. Bioorg. Med. Chem. 2009; 17: 1276
• 2b Heng S, Gryncel KR, Kantrowitz ER. Bioorg. Med. Chem. 2009; 17: 3916
• 2c Copp BR. Nat. Prod. Rep. 2003; 20: 535
• 3a Kato Y, Fusetani N, Matsunaga S, Hashimoto K, Fujita S, Furuya T. J. Am. Chem. Soc. 1986; 108: 2780
• 3b Adamczeski M, Quinoa E, Crews P. J. Am. Chem. Soc. 1988; 110: 1598
• 3c Ichiba T, Yoshida WY, Scheuer PJ, Higa T, Gravalos DG. J. Am. Chem. Soc. 1991; 113: 3173
• 3d Searle PA, Molinski TF. J. Am. Chem. Soc. 1995; 117: 8126
• 3e Ishibashi Y, Ohba S, Nishiyama S, Yamamura S. Tetrahedron Lett. 1996; 37: 2997
• 3f Sandler JS, Colin PL, Kelly M, Fenical W. J. Org. Chem. 2006; 71: 7245
• 3g Chakraborty TK, Pulukuri KK, Sreekanth M. Tetrahedron Lett. 2010; 51: 6444
• 3h Eto K, Yoshino M, Takahashi K, Ishihara J, Hatakeyama S. Org. Lett. 2011; 13: 5398
• 3i Larivée A, Unger JB, Thomas M, Wirtz C, Dubost C, Handa S, Fürstner A. Angew. Chem. Int. Ed. 2011; 50: 304
• 3j Jing Z. Nat. Prod. Rep. 2013; 30: 869
• 4a Bonne D, Dekhane M, Zhu JP. Angew. Chem. Int. Ed. 2007; 46: 2485
• 4b Williams DR, Fu L. Org. Lett. 2010; 12: 808
• 4c Ohnmacht SA, Mamone P, Culshaw AJ, Greaney MF. Chem. Commun. 2008; 44: 1241
• 4d Shi B, Blake AJ, Lewis W, Campbell IB, Judkins BD, Moody CJ. J. Org. Chem. 2010; 75: 152
• 4e Pan YM, Zheng FJ, Lin HX, Zhan ZP. J. Org. Chem. 2009; 74: 3148
• 4f Saito A, Iimura K, Hanzawa Y. Tetrahedron Lett. 2010; 51: 1471
• 5a Nicolaou KC, Hao J, Reddy MV, Rao PB, Rassias G, Snyder SA, Huang X, Chen DY, Brenzovich WE, Giuseppone N, Giannakakou P, O’Brate A. J. Am. Chem. Soc. 2004; 126: 12897
• 5b Lechel T, Lentz D, Reissig HU. Chem. Eur. J. 2009; 15: 5432
• 5c Takeuchi H, Yanagida S, Ozaki T, Hagiwara S, Eguchi S. J. Org. Chem. 1989; 54: 431
• 5d Keni M, Tepe JJ. J. Org. Chem. 2005; 70: 4211
• 5e Wipf P, Miller CP. J. Org. Chem. 1993; 58: 3604
• 5f Wendlandt AE, Stahl SS. Org. Biomol. Chem. 2012; 10: 3866
• 5g Cordero FM, Giomi D, Lascialfari L. Prog. Heterocycl. Chem. 2013; 25: 291
• 6a Wan C, Zhang J, Wang S, Fan J, Wang Z. Org. Lett. 2010; 12: 2338
• 6b Wan CF, Gao LF, Wang Q, Zhang JT, Wang ZY. Org. Lett. 2010; 12: 3902
• 6c Xue WJ, Li Q, Zhu YP, Wang JG, Wu AX. Chem. Commun. 2012; 48: 3485
• 6d Xie J, Jiang H, Cheng Y, Zhu C. Chem. Commun. 2012; 48: 979
• 6e Fu LF. Top. Heterocycl. Chem. 2012; 29: 103
• 7a Meyers AI, Tavares F. Tetrahedron Lett. 1994; 35: 2481
• 7b Phillips AJ, Uto Y, Wipf P, Reno MJ, Williams DR. Org. Lett. 2000; 2: 1165
• 7c Meyers AI, Tavares FX. J. Org. Chem. 1996; 61: 8207
• 7d Williams DR, Lowder DP, Gu GY, Brooks DA. Tetrahedron Lett. 1997; 38: 331
• 7e Wang Y, Li Z, Huang Y, Tang C, Wu X, Xu J, Yao H. Tetrahedron 2011; 67: 7406
• 7f Huang Y, Ni L, Gan F, He Y, Xu J, Wu X, Yao H. Tetrahedron 2011; 67: 2066
• 7g Babaev EV. Chem. Heterocycl. Comp. 2012; 48: 59
• 8a Cano I, Alvarez E, Nicasio CM, Perez PJ. J. Am. Chem. Soc. 2011; 133: 191
• 8b Lee JC, Kim S, Lee YC. Synth. Commun. 2003; 33: 1611
• 8c Nesi R, Turchi S, Giomi D. J. Org. Chem. 1996; 61: 7933
• 8d Mendelsohn BA, Lee S, Kim S, Teyssier F, Aulakh VS, Ciufolini MA. Org. Lett. 2009; 11: 1539
• 8e Zhong CL, Tang BY, Yin P, Chen Y, He L. J. Org. Chem. 2012; 77: 4271
• 8f Ferrini PG, Marxer A. Angew. Chem. Int. Ed. 1963; 2: 98
• 8g Merkul E, Muller TJ. J. Chem. Commun. 2006; 42: 4817
• 8h Young GL, Smith SA, Taylor RJ. K. Tetrahedron Lett. 2004; 45: 3797
• 8i Lister J, Robinson R. J. Chem. Soc. 1912; 101: 1297
• 8j Kumar MP, Liu R.-S. J. Org. Chem. 2006; 71: 4951
• 8k Kison C, Opatz T. Chem. Eur. J. 2009; 15: 843
• 8l Shi B, Blake AJ, Lewis W, Campbell IB, Judkins BD, Moody CJ. J. Org. Chem. 2010; 75: 152
• 8m Jiang H, Huang H, Cao H, Qi C. Org. Lett. 2010; 12: 5561
• 8n Pan YM, Zheng FJ, Lin HX, Zhan ZP. J. Org. Chem. 2009; 74: 3148
• 8o Lee JJ, Kim J, Jun YM, Lee BM, Kim BH. Tetrahedron 2009; 65: 8821
• 8p Coqueron P.-Y, Didier C, Ciufolini MA. Angew. Chem. Int. Ed. 2003; 42: 1411
• 8q Li X, Huang L, Chen H, Wu W, Huang H, Jiang H. Chem. Sci. 2012; 3: 3463
• 9a Kinjo R, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2011; 50: 5560
• 9b Zheng QW, Hua RM. Tetrahedron Lett. 2010; 51: 4512
• 9c Wang LG, Yu XQ, Feng XJ, Bao M. J. Org. Chem. 2013; 78: 1693
• 9d Lavallo V, Frey GD, Donnadieu B, Soleilhavoup M, Bertrand G. Angew. Chem. Int. Ed. 2008; 47: 5224
• 10a Kramer S, Madsen JL. H, Rottlander M, Skrydstrup T. Org. Lett. 2010; 12: 2758
• 10b Nun P, Dupuy S, Gaillard S, Poater A, Cavallo L, Nolan SP. Catal. Sci. Technol. 2011; 1: 58
• 10c Pérez JM, Cano R, Yus M, Ramón DJ. Synthesis 2013; 45: 1373
• 11a Okamoto T, Kudoh K, Wakamiya A, Yamaguchi S. Org. Lett. 2005; 7: 5301
• 11b Jiang HF, Zeng W, Li YB, Wu WQ, Huang LB, Fu W. J. Org. Chem. 2012; 77: 5179
• 11c Potta KT, Nye SA, Smith KA. J. Org. Chem. 1992; 57: 3895
• 12a For Au-catalyzed heterocyclizations, see: He W, Li C, Zhang L. J. Am. Chem. Soc. 2011; 133: 8482
• 12b For Cu-catalyzed heterocyclizations, see: Li XW, Huang LB, Chen HJ, Wu WQ, Huang HW, Jiang HF. Chem. Sci. 2012; 3: 3463
• 13 Saito A, Taniguchi A, Kambara Y, Hanzawa Y. Org. Lett. 2013; 15: 2672
• 14a Tang JL, Zhao XM. RSC Adv. 2012; 2: 5488
• 14b Tang JL, Ming L, Zhao XM. Synthesis 2013; 45: 1713
• 15 Wang LG.. Yu X. Q, Feng XJ, Bao M. Org. Lett. 2012; 14: 2418
• 16a Zhang SL, Liu XY, Wang TQ. Adv. Synth. Catal. 2011; 353: 1463
• 16b Yin WY, He C, Chen M, Zhang H, Lei AW. Org. Lett. 2009; 11: 709
• 16c Zheng QW, Hua RM, Wan YZ. Appl. Organomet. Chem. 2010; 24: 314
• 16d Wang D, Li JH, Li N, Gao TT, Hou SH, Chen BH. Green Chem. 2010; 12: 45
• 16e Sugiyama J, Tomita I. Eur. J. Org. Chem. 2007; 4651