Diastereoselective Synthesis of Novel and Enantiopure Tetrahydropyrano[3,2-c]quinolines

Abstract

Diastereoselective synthesis of novel and enantiopure N-alkylated tetrahydropyrano[3,2-c]quinolines is described via intramolecular Friedel–Crafts alkylation using a 1-O-acetylglucosyl derivative as the key intermediate. Unprecedented formation of new glycal derivatives and α,β-unsaturated carbaldehyde products is also discussed.

Key words

tetrahydropyrano[3,2-c]quinoline - Friedel–Crafts alkylation - Povarov reaction - glucal - scandium triflate

• References

• 1 Sridharan V, Suryavanshi PA, Menéndez JC. Chem. Rev. 2011; 111: 7157
• 2 Camps P, Formosa X, Galdeano C, Muñoz-Torrero D, Ramírez L, Gómez E, Isambert N, Lavilla R, Badia A, Clos MV, Bartolini M, Mancini F, Andrisano V, Arce MP, Rodríguez-Franco MI, Huertas Ó, Dafni T, Luque FJ. J. Med. Chem. 2009; 52: 5365
• 3 Palaniappan S, Rajender B, Umashankar M. J. Mol. Catal. A: Chem. 2012; 352: 70 ; and references cited therein
• 4 Majumdar KC, Ponra S, Ghosh T, Sadhukhan R, Ghosh U. Eur. J. Med. Chem. 2014; 71: 306
• 5 Ghorab MM, Abdel-Hamide SG, Farrag HA. Acta Pol. Pharm. 2001; 58: 175
• 6 Reddy BV. S, Grewal H. Tetrahedron Lett. 2011; 52: 761
• 7 Majumdar KC, Ponra S, Ghosh T. Tetrahedron Lett. 2013; 54: 5586
• 8 Zhang Q, Zhang Z, Yan Z, Liu Q, Wang T. Org. Lett. 2007; 9: 3651
• 9 Nagarapu L, Bantu R, Puligoundla RG. Eur. J. Chem. 2011; 2: 260 ; http://www.eurjchem.com/index.php/eurjchem
• 10 Reddy BV. S, Medaboona D, Sridhar B, Singarapu KK. J. Org. Chem. 2013; 78: 8161
• 11 Yadav JS, Reddy BV. S, Sadasiv K, Reddy PS. R. Tetrahedron Lett. 2002; 43: 3853
• 12 Jin G, Zhao J, Han J, Zhu S, Zhang J. Tetrahedron 2010; 66: 913
• 13 Zhang J, Li C.-J. J. Org. Chem. 2002; 67: 3969
• 14 Chen R, Qian C. Synth. Commun. 2002; 32: 2543
• 15 Yadav JS, Reddy BV. S, Parimala G, Raju AK. Tetrahedron Lett. 2004; 45: 1543
• 16 Rafiee E, Azad A. Bioorg. Med. Chem. Lett. 2007; 17: 2756
• 17 Yadav JS, Reddy BV. S, Srinivas M, Padmavani B. Tetrahedron 2004; 60: 3261
• 18 Yadav JS, Reddy BV. S, Rao KV, Raj KS, Prasad AR, Kumar SK, Kunwar AC, Jayaprakash P, Jagannath B. Angew. Chem. Int. Ed. 2003; 42: 5198
• 19 Jiménez O, de la Rosa G, Lavilla R. Angew. Chem. Int. Ed. 2005; 44: 6521
• 20 Kumar A, Srivastava S, Gupta G, Chaturvedi V, Sinha S, Srivastava R. ACS Comb. Sci. 2011; 13: 65
• 21 Povarov LS. Russ. Chem. Rev. 1967; 36: 656
• 22 Fochi M, Caruana L, Bernardi L. Synthesis 2014; 46: 135
• 23 Caruana L, Fochi M, Ranieri S, Mazzanti A, Bernardi L. Chem. Commun. 2013; 49: 880
• 24 Min C, Sanchawala A, Seidel D. Org. Lett. 2014; 16: 2756
• 25 Sundararajan G, Prabagaran N, Varghese B. Org. Lett. 2001; 3: 1973
• 26 Ishitani H, Kobayashi S. Tetrahedron Lett. 1996; 37: 7357
• 27 Akiyama T, Morita H, Fuchibe K. J. Am. Chem. Soc. 2006; 128: 13070
• 28 Kinfe HH, Moshapo PT, Makolo FL, Muller A. J. Carbohydr. Chem. 2013; 32: 139
• 29 Kinfe HH, Makolo FL, Moshapo PT, Phasha ZH. J. Carbohydr. Chem. 2013; 32: 193
• 30 Kinfe HH, Mebrahtu FM, Makolo FL, Moshapo PT, Manana MM. J. Org. Chem. 2014; 79: 3111
• 31 Kinfe HH, Makolo FL, Adokoh CK. J. Org. Chem. 2014; 79: 7718
• 32 Kinfe HH, Moshapo PT, Makolo FL, Gammon DW, Ehlers M, Schmuck C. Eur. J. Med. Chem. 2014; 87: 197
• 33 Kinfe HH, Mebrahtu FM, Manana MM, Madumo K, Sokamisa MS. Beilstein J. Org. Chem. 2015; 11: 583
• 34 Salvatore RN, Yoon CH, Jung KW. Tetrahedron 2001; 57: 7785
• 35 Abdallah Z, Doisneau G, Beau JM. Angew. Chem. Int. Ed. 2003; 42: 5209
• 36 Perrin DD, Armarego LF. Purification of Laboratory Chemicals . 3rd ed. Pergamon Press; Oxford: 1988
• 37 Gammon DW, Kinfe HH, De Vos DE, Jacobs PA, Sels BF. J. Carbohydr. Chem. 2007; 26: 141
• 38 Ramana CV, Murali R, Nagarajan M. J. Org. Chem. 1997; 62: 7694