References
- Eskici, M.; Karanfil, A.; Özer, M. S.; Sarıkürkcü, C. Tetrahedron Lett. 2011, 52, 6336–6341.
- (a) Melendez, R. E.; Lubel, W. D. Tetrahedron 2003, 59, 2581–2616; (b) Bower, J. F.; Rujirawanich, J.; Gallagher, T. Org. Biomol. Chem. 2010, 8, 1505–1519.
- For selected examples of generation and use of lithiumalkylpropiolate, see: (a) Shekhar, V.; Reddy, D. K.; Suresh, V.; Babu, D. C.; Venkateswarlu, Y. Tetrahedron Lett. 2010, 51, 946–948; (b) Yaragorla, S.; Muthyala, R. Tetrahedron Lett. 2010, 51, 467–470; (c) Yadav, J. S.; Rao, M.; Sanjeevarao, K.; Reddy, B. V. S. Synlett 2008, 1039–1041; (d) Ma, D.; Xie, W.; Zou, B.; Lei, Q.; Pei, D. Tetrahedron Lett. 2004, 45, 8103–8105; (e) Crimmins, M. T.; Pace, J. M.; Nantermet, P. G.; Kim-Meade, A. S.; Thomas, J. B.; Watterson, S. H.; Wagman, A. S. J. Am. Chem. Soc. 2000, 122, 8453–8463; (f) Mancini, I.; Guella, G.; Guerriero, A.; Boldrin, A.; Pietra, F. Helv. Chim. Acta 1987, 70, 2011–2018; (g) Hirama, M.; Shigemato, T.; Ito, S. J. Org. Chem. 1987, 52, 3342–3346; (h) Tejedor, D.; Lopez-Tosco, S.; Cruz-Acosta, F.; Mendez-Abt, G.; Garcia-Tellado, F. Angew. Chem. Int. Ed. 2009, 48, 2090–2098.
- (a) Stetter, H.; Uerdingen, W. Synthesis 1973, 4, 207–208; (b) Bates, R. W.; Maiti, T. B. Synth. Commun. 2003, 33, 633–640.
- (a) Boche, G.; Bigalke, J. Tetrahedron Lett. 1984, 25, 955–958; (b) Shattuck, J. C.; Svatog, A.; Blazey, C. M.; Meinwald, J. Tetrahedron Lett. 1997, 38, 6803–6806; (c) Mames, A.; Stecko, S.; Mikołajczyk, P.; Soluch, M.; Furman, B.; Chmielewski, M. J. Org. Chem. 2010, 75, 7580–7587.
- Gassman, P. G.; Chavan, S. P. Tetrahedron Lett. 1988, 29, 3407–3410.
- Armengol, M.; Joule, J. A. J. Chem. Soc. Perkin Trans. 2001, 1, 978–984; The synthesis of 3,3,3-triethoxypropyne 9 using the similar reagents and conditions in comparable yields is also given in PhD thesis by Montserrat Armengol, “The synthesis of thieno[2,3-b]quinoxalines and quinoxalines with extended conjugation”, University of Manchester, UK, 2001. As this material is not published in main stream journals, it is not easily accessible. Therefore several additional useful observations for practical synthesis of 9 in large quantities and high purity are presented in this communication.
- Frame, R. R.; Faulconer, W. J. Org. Chem. 1971, 36, 2048–2050.
- Feugeas, C.; Giusti, G. C. R. Acad. Sci., Ser. C 1967, 264, 1772–1774; (b) Giusti, G. Bull. Soc. Chim. Fr. 1972, 753–758.
- (a) Henrick, C. A.; Willy, W. E.; Garcia, B. A.; Staal, G. B. J. Agric. Food Chem. 1975, 23, 396–400; (b) Ando, K.; Houk, K. N.; Busch, J.; Menasse, A.; Sequin, U. J. Org. Chem. 1998, 63, 1761–1766.
- Uemura, S.; Fukuzawa, S.-I. J. Chem. Soc. Perkin Trans. 1986, 1, 1983–1987.
- Knowles, J. P.; Whitting, A. Eur. J. Org. Chem. 2007, 3365–3368.
- Karanfil, A.; Balta, B.; Eskici, M. Tetrahedron 2012, 68, 10218–10229.