Anionic Cyclization of (N,N-Dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles

Abstract

The cyclization of (N,N-dimethylamino)[2-(prop-2-yn-1-yloxy)aryl]acetonitriles is carried out under phase-transfer conditions using powdered sodium hydroxide and benzyltriethylammonium chloride as catalyst in dimethyl sulfoxide to afford mixtures of a methylenechromane and a methylchromene via favored 6-exo-dig and 6-endo-dig processes, respectively. Several of the chromenes rearranged into benzofuranone derivatives during column chromatography on alumina and the formation of these is rationalized.

Key words

phase-transfer catalysis - carbanions - cyclizations - heterocycles - intramolecular vinylation

References

• 1 Baldwin JE. J. Chem. Soc., Chem. Commun.  1976,  734 
• 2 Eglington G. Whiting MC. J. Chem. Soc.  1953,  3052 
• 3 Mavrov MV. Kutcherov VF. Izv. Akad. Nauk SSSR, Ser. Khim.  1964,  1653 
• 4 Mavrov MV. Dierzinskii AR. Kutcherov VF. Izv. Akad. Nauk SSSR, Ser. Khim.  1965,  1460 
• 5 Kitagawa O. Suzuki T. Fujiwara H. Fujita M. Taguchi T. Tetrahedron Lett.  1999,  40:  4585 
• 6 Mavrov MV. Kutcherov VF. Izv. Akad. Nauk SSSR, Ser. Khim.  1964,  1820 
• 7 MaGee DI. Leach JD. Setiadji S. Tetrahedron  1999,  55:  2847 
• 8 Vieser R. Eberbach W. Tetrahedron Lett.  1995,  36:  4405 
• 9 Arcadi A. Marinelli F. Pini E. Rossi E. Tetrahedron Lett.  1996,  37:  3387 
• 10 Makra F. Rohloff JC. Muehldorf AV. Link JO. Tetrahedron Lett.  1995,  36:  6815 
• 11 Jackson-Mülly M. Zsindely J. Schmid H. Helv. Chim. Acta  1976,  69:  664 
• 12 Arcadi A. Cacchi S. Fabrizi G. Marinelli F. Synlett  1993,  65 
• 13 Arcadi A. Cacchi S. Fabrizi G. Manna F. Pace P. Synlett  1998,  446 
• 14 Patra R. Maiti SB. Chatterjee A. Chakravarty AK. Tetrahedron Lett.  1991,  32:  1363 
• 15 Lavoisier-Gallo T. Rodriguez J. J. Org. Chem.  1997,  62:  3787 
• 16 Wang J.-L. Ueng C.-H. Yeh M.-CP. Tetrahedron Lett.  1995,  36:  2823 
• 17 Koradin C. Rodriguez A. Knochel P. Synlett  2000,  1452 
• 18 Dehmlow EW. Dehmlow SS. Phase Transfer Catalysis   3rd ed.:  Wiley-VCH; Weinheim: 1993. 
• 19 Starks CM. Liotta ML. Halpern M. Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives   Chapman & Hall; New York / London: 1994. 
• 20 Mąkosza M. Fedoryński M. Catal. Rev.  2003,  45:  321 
• 21 Mąkosza M. Serafinowa B. Bolesawska B. Rocz. Chem.  1968,  42:  817 
• 22 Mąkosza M. Tetrahedron Lett.  1966,  5489 
• 23 Jończyk A. Lipiak D. Zdrojewski T. Tetrahedron  1990,  46:  102 
• 24 Zdrojewski T. Jończyk A. Synthesis  1990,  224 
• 25 Zdrojewski T. Jończyk A. Liebigs Ann. Chem.  1993,  375 
• 26 Jończyk A. Pakulski Z. Tetrahedron Lett.  1996,  37:  8909 
• 27 Wittig G. Blumenthal H. Chem. Ber.  1927,  60B:  1085 
• 28 Lockhart IM. Tanner EM. J. Chem. Soc.  1965,  3610 
• 29 Janietz D. Rudorf W.-D. Tetrahedron  1989,  45:  1661