Green chemistry approaches to the regioselective synthesis of spiro heterobicyclic rings using iodine as a new and efficient catalyst under solvent-free conditions

Biginelli P (1893) Synthesis of tetrahydropyrimidinones by the acid catalyzed condensation of an aldehyde, a β-ketoester and urea. Gazz Chim Ital 23: 360–416 Yarim M, Sarac S, Kilic FS, Erol K (2003) Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyls1,7, 7,-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives. Il Farmaco 58: 17–24. doi:10.1016/S0014-827X(02)00009-5 Byk G, Gettlieb HE, Herscovici J, Mirkin F (2000) New regioselective multicomponent reaction: One pot synthesis of spiro heterocyclic aliphatic rings. J Comb Chem 2: 732–735. doi:10.1021/cc000056p Mokrosz JL, Paluchowska MH, Szneler E, Drozdz B (1989) The effect of aryl substituents in some spiro[2-oxo-4,6-bis(aryl)hexahydropyrimidine-5,5′-barbituric acids]. Arch Chem (Weinheim, Germany) 322: 231–235 Mamaev VP, Borovik VP (1968) Spiro[2-oxo-4,6-bis(aryl)hexahydropyrimidine-5,5′-barbituric acids]. Izobret Prom Obraztsy Tovarnye Znaki 45:24; Chem Absrt 69: 96790f Borovik VP, Mamaev VP (1970) Synthesis of sulfur-containing spiropyrimidine barbituric acids. Kim Farm Zh 4:32–35; Chem Abstr 72:111411 Abelman MM, Smith SC, James DR (2003) Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold synthesis. Tetrahedron Lett 44: 4559–4562. doi:10.1016/S0040-4039(03)00985-7 Field KW, Wilder D, Utz A, Kolb KE (1987) Addition of Iodine to alkenes: A pseudo first-, second-, or third-order kinetics experiment. J Chem Educ 64: 269–270. doi:10.1021/ed064p269 Klein J (1959) The Iodolactonization of Cyclohexaneacetic Acids. J Am Chem Soc 81: 3611–3614. doi:10.1021/ja01523a035 Freiberg LA (1967) Mechanism of oxidation of enolizable nonmethyl ketones by base and iodine. The role of atmospheric oxygen. J Am Chem Soc 89: 5297–5298. doi:10.1021ja00996a045 Kirk KC (1978) Facile synthesis of 2-substituted imidazoles. J Org Chem 43: 4381–4383. doi:10.1021jo00416a033 Brown HC, Rathke MW, Rogic MM, DeLue NR (1988) Organoboranes for synthesis. 9. Rapid reaction of organoboranes with iodine under the influence of base. A convenient procedure for the conversion of alkenes into iodides via hydroboration. Tetrahedron 44: 2751–2762. doi:10.1016/S0040-4020(88)90010-5 Zweifel G, Fisher RP, Snow JT, Whitney CC (1972) Convenient synthesis of trans olefins from alkynes via hydroboration-cyanohalogenation. J Am Chem Soc 94: 6560–6561. doi:10.1021/ja00773a059 Shaabani A, Bazagir A (2004) Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions. Tetrahedron Lett 45: 2575–2577. doi:j.tetlet.2004.01.154 Santagada V, Frecentese F, Perissutti E, Favretto L, Caliendo G (2004) The application of microwaves in combinatorial and high-throughput synthesis as new synthetic procedure in drug discovery. QSAR Comb Sci 23: 919–944. doi:10.1002/qsar.200420039 Choudhary VR, Tillu VH, Narkhede VS, Borate HB, Wakhardar RD (2003) Microwave assisted solvent-free synthesis of dihydropyrimidinones by Biginelli reaction over Si-MCM-41 supported FeCl3 catalyst. Cat Commun 4: 449–453. doi:10.1016/S1566-7367(03)/00111-0 Kuhnert N (2002) Microwave-assisted reactions in organic synthesis—Are there any nonthermal microwave effects?. Angew Chem Int Edn 41: 1863–1866. doi:10.1002/1521-3773(20020603)41:11<1863 Manufactured by M/s Prolabo, 54 rue Roger Salengro; F-94126 Fontenay-Sous-Bois, Cedix-France, Tel: 01 45 14 85 00; Fax: 01 45 14 85 15; Fax Export: 33 145148616 Kappe CO (1997) A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate. J Org Chem 62: 7201–7204. doi:10.1021/jo971010u Folkers K, Johnson TB (1933) Researches on pyrimidines. CXXXVI. The mechanism of formation of tetrahydropyrimidines by the Biginelli reaction. J Am Chem Soc 55: 3784–3791. doi:10.1021/ja01336a053 Kaup G, Reza Naim MJ, Schmeyers J (2003) Sovent free Knoevenagel condensation and Michael additions in the solid state and in the melt with quantitative yield. Tetrahedron 59: 3753–3760. doi:10.1016/S0040-4020(03)00554-4