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

Molecular Diversity

Volumn 15, Issue 1, 2011, Pages 257-261

  Prajapati, Dipak ^a   Bhuyan, Debajyoti ^a   Gohain, Mukut ^a   Hu, Wenhao ^b  

^a Medicinal Chemistry Division   (India)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

1, 3 dicarbonyl compounds; Barbituric acid; Biginelli like reaction; Iodine; MCR; Microwave synthesis; Multicomponent; Spiro fused heterocycles

Indexed keywords

ALDEHYDE DERIVATIVE; BARBITURIC ACID; BARBITURIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; IODINE; SPIRO(2 OXO 4,6 DIPHENYLHEXAHYDROPYRIMIDINE 5,5' BARBITURIC ACID); SPIRO[2 OXO 4,6 DIPHENYLHEXAHYDROPYRIMIDINE 5,5' (1' METHYLBARBITURIC ACID)]; UNCLASSIFIED DRUG; UREA;

ARTICLE; BIGINELLI REACTION; CATALYST; GREEN CHEMISTRY; MICROWAVE IRRADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; GREEN CHEMISTRY TECHNOLOGY; IODINE; MICROWAVES; SOLVENTS; SPIRO COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 79953321078     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-010-9247-4     Document Type: Article

References (23)

1. 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
2. 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
3. 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
4. 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 (Pubitemid 19097421)
5. Mamaev VP, Borovik VP (1968) Spiro[2-oxo-4,6-bis(aryl) hexahydropyrimidine-5,5′-barbituric acids]. Izobret Prom Obraztsy Tovarnye Znaki 45:24;
6. Chem Absrt 69: 96790f
7. Borovik VP, Mamaev VP (1970) Synthesis of sulfur-containing spiropyrimidine barbituric acids. Kim Farm Zh 4:32-35;
8. Chem Abstr 72:111411
9. 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 (Pubitemid 36588630)
10. 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
11. Klein J (1959) The Iodolactonization of Cyclohexaneacetic Acids. J Am Chem Soc 81:3611-3614. doi:10.1021/ja01523a035
12. 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
13. Kirk KC (1978) Facile synthesis of 2-substituted imidazoles. J Org Chem 43:4381-4383. doi:10.1021jo00416a033
14. 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
15. Zweifel G, Fisher RP, Snow JT, Whitney CC (1972) Convenient synthesis of trans olefins from alkynes via hydroborationcyanohalogenation. J Am Chem Soc 94:6560-6561. doi:10.1021/ja00773a059
16. 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
17. 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 (Pubitemid 40127767)
18. 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 (Pubitemid 41087748)
19. KuhnertN (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
20. 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
21. 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
22. 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
23. 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