VCl 3 catalyzed imine-based multicomponent reactions for the facile access of functionalized tetrahydropyridines and β-amino carbonyls

Molecular Diversity

Volumn 16, Issue 1, 2012, Pages 129-143

  Pal, Suman ^a   Choudhury, Lokman Hakim ^a   Parvin, Tasneem ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY PATNA   (India)

Author keywords

Amino carbonyls; MCRs; Multicomponent reactions; Tetrahydropyridines; VCl 3

Indexed keywords

1 (4 BROMOPHENYL) 3 (4 CHLOROPHENYL) 3 (4 NITRO PHENYL AMINO)PROPAN 1 ONE; 1 (4 BROMOPHENYL) 3 (4 CHLOROPHENYLAMINO) 3 PHENYLPROPAN 1 ONE; 1 (4 BROMOPHENYL) 3 PHENYL 3 (PHENYLAMINO)PROPAN 1 ONE; 1 PHENYL 3 (PHENYLAMINO) 3 4 TOLYLPROPAN 1 ONE; 1,3 DIPHENYL 3 (4 TOLYLAMINO)PROPAN 1 ONE; 1,3 DIPHENYL 3 (PHENYLAMINO)PROPAN 1 ONE; 3 (4 CHLOROPHENYL) 3 (4 NITROPHENYLAMINO) 1 PHENYLPROPAN ONE; 3 (4 CHLOROPHENYLAMINO) 1,3 DIPHENYLPROPAN 1 ONE; 3 (4 CHLOROPHENYLAMINO) 3 (4 METHOXYPHENYL) 1 PHENYLPROPAN 1 ONE; 3 (4 METHOXYPHENYL) 1 PHENYL 3 (PHENYLAMINO)PROPAN 1 ONE; 3 (4 NITROPHENYLAMINO) 1,3 DIPHENYLPROPAN 1 ONE; 4 (3 OXO 1,3 DIPHENYLPROPYLAMINO)BENZONITRILE; ALDEHYDE; CARBONYL DERIVATIVE; IMINE; KETONE; LEWIS ACID; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; VANADIUM DERIVATIVE; ACETOPHENONE DERIVATIVE; AMINE;

ARTICLE; ATOM; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; MANNICH REACTION; PRIORITY JOURNAL; SYNTHESIS; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY;

ACETOPHENONES; ALDEHYDES; AMINES; CATALYSIS; CHEMISTRY, ORGANIC; IMINES; PYRIDINES; VANADIUM COMPOUNDS;

EID: 84858701265     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9339-9     Document Type: Article

References (49)

1. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-89. doi:10.1021/cr0505728
2. Zhu J, Bienaymé H (2005) Multicomponent reactions; Eds. Wiley-VCH, Weinheim
3. Tempest PA (2005) Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction. Curr Opin Drug Disc Dev 8:776-788
4. Clarke PA, Zaytsev AV, Whitwood AC (2008) Pot, atom, and step economic (PASE) synthesis of highly substituted piperidines: A five-component condensation. Synthesis 3530-3532. doi:10.1055/s-0028-1083182
5. Clarke PA, Zaytsev AV, Morgan TW, Whitwood AC, Wilson C (2008) One-pot synthesis of functionalized piperid-4-ones: a four-component condensation. Org Lett 10:2877-2880. doi:10.1021/ol801051g
6. Dhawan R, Dghaym RD, Cyr DJS, Arndtsen BA (2006) Direct, palladium-catalyzed, multicomponent synthesis of β-Lactamsfrom imines, acid chloride, and carbon monoxide.Org Lett 8:3927-3930. doi:10.1021/ol061308j (Pubitemid 44432822)
7. Black DA, Arndtsen BA (2005) Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: A multicomponent synthesis of α-substituted amides. J Org Chem 70:5133-5138. doi:10.1021/jo0503557 (Pubitemid 40863916)
8. Lu Y, Arndtsen BA (2009) A direct phosphine-mediated synthesis of pyrroles from acid chlorides and α, β-unsaturated imines. Org Lett 11:1369-1372. doi:10.1021/ol900185n
9. Maiti S, Biswas S, Jana U (2010) Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: A simple and direct synthesis of functionalized pyrroles. J Org Chem 75:1674-1683. doi:10.1021/jo902661y
10. Worrall K, Xu B, Bontemps S, Arndtsen BA (2010) A palladium-catalyzed multicomponent synthesis of imidazolinium salts and imidazolines from imines, acid chlorides, and carbon monoxide. J Org Chem 76:170-180. doi:10.1021/ jo101858d
11. Choudhury LH, Parvin T (2011) Recent advances in the chemistry of imine based-multicomponent reactions. Tetrahedron 67:8213-8228. doi:10.1016/j.tet. 2011.07.020
12. 2O-mediated grob fragmentation: access to indolizidines (-)-209I and (-)-223J. J Org Chem 75:7465-7467. doi:10.1021/jo1015344
13. Zhu XF, Lan J, Kwon O (2003) An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines. J Am Chem Soc 125:4716-4717. doi:10.1021/ja0344009 (Pubitemid 36505358)
14. Glase SA, Akunne HC, Heffner TG, Jaen JC, MacKenzie RG, Meltzer LT, Pugsley TA, Smith SJ, Wise LD (1996) Aryl 1-but- 3-ynyl-4-phenyl-1,2,3,6- tetrahydropyridines as potential antipsychotic agents: synthesis and structure-activity relationships. J Med Chem 39:3179-3187. doi:10.1021/jm950721m (Pubitemid 26260324)
15. Finke PE, Oates B, Mills SG, MacCoss M, Malkowitz L, Springer MS, Gould SL, Demartino JA, Carella A, Carver G, Holmes K, Danzeisen R, Hazuda D, Kessler J, Lineberger J, Miller M, Schleif WA, Emini EA (2001) Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 4: synthesis and structure-activity relationships for 1-[N-(Methyl)-N-(phenylsulfonyl) amino]-2-(phenyl)-4-(4-(N- (alkyl)-(benzyloxycarbonyl) amino) piperidin-1-yl) butanes. Bioorg Med Chem Lett 11:2475-2479. doi:10.1016/S0960-894X(01)00492-9
16. Trabaco AA,Aerts N, AlvarezRM, Andres JI,Boeckx I, Fernandez J, Gomez A, Janssens FE, Leenaerts JE, Lucas AID, Matesanz E, Steckler T, Pullan S (2007) 4-Phenyl-4-[1H-imidazol- 2-yl]-piperidine derivatives as non-peptidic selective δ-opioid agonists ith potential anxiolytic /antidepressant properties. Part 2. Bioorg Med Chem Lett 17:3860-3863. doi:10.1016/j.bmcl.2007.05.012 (Pubitemid 46920955)
17. Misra M, Pandey SK, Pandey VP, Pandey V, Tripathi RP (2009) Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials.BioorgMed Chem 17:625-633. doi:10.1016/j.bmc.2008.11.062
18. Tsukamoto H, Kondo Y (2008) Palladium(0)-catalyzed alkynyl and allenyl iminium ion cyclizations leading to 1,4-disubstituted 1,2,3,6- tetrahydropyridines. Angew Chem Int Ed 47:4851-4854. doi:10.1002/anie.200800823
19. Han RG, Wang Y, Li YY, Xua PF (2008) Proline-mediated enantioselective construction of tetrahydropyridines via a cascadeMannich- type/intramolecular cyclization reaction. Adv Synth Catal 350:1474-1478. doi:10.1002/adsc.200800253
20. Lee HS, Kim ES, Kim SH, Kim JN (2009) Synthesis of poly-substituted tetrahydropyridines from Baylis-Hillman adducts modified with N-allylamino group via radical cyclization. Tetrahedron Lett 50:2274-2277. doi:10.1016/j.tetlet. 2009.02.225
21. Takizawa S, Inoue N, Sasai H (2011) An enantioselective organocatalyzed aza-MBH domino process: application to the facile synthesis of tetrahydropyridines. Tetrahedron Lett 52:377-380. doi:10.1016/j.tetlet.2010.11. 045
22. Clarke PA, Zaytzev AV, Whitwood AC (2007) Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation. Tetrahedron Lett 48:5209-5212. doi:10.1016/j.tetlet.2007.05.141 (Pubitemid 46977005)
23. Khan AT, Parvin T, Choudhury LH (2008) Effects of substituents in the β-Position of 1,3-dicarbonyl compounds in bromodimethylsulfonium bromide-catalyzed multicomponent reactions: A facile access to functionalized piperidines. J Org Chem 73:8398-8402. doi:10.1021/jo8014962
24. Khan AT, Lal M, Khan MM (2010) Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB). Tetrahedron Lett 51:4419-4424. doi:10.1016/j.tetlet.2010.06. 069
25. Khan AT, Khan MM, Bannuru KKR (2010) Iodine catalyzed onepot five-component reactions for direct synthesis of densely functionalized piperidines. Tetrahedron 66:7762-7772. doi:10.1016/j.tet.2010.07.075
26. Wang H-J, Mo L-P, Zhang Z-H (2011) Cerium ammonium nitrate-catalyzed multicomponent reaction for efficient synthesis of functionalized tetrahy dropyridines. ACS Comb Sci 13:181-185. doi:10.1021/co100055x
27. 2O catalyzed tandem reactions of aromatic aldehydeswith amines and acetoacetic esters. Tetrahedron Lett 52:2857-2861. doi:10.1016/j.tetlet.2011.03.116
28. Sabitha G, Reddy GSKK, Reddy KB, Yadav JS (2003) Vanadium(III) chloride catalyzed Biginelli condensation: solution phase library generation of dihydropyrimidin-(2H)-ones. Tetrahedron Lett 44:6497-6499. doi:10.1016/S0040- 4039(03)01564-8 (Pubitemid 36936949)
29. Sabitha G, Reddy GSKK, Reddy KB, Yadav JS (2003) Vanadium(III) chloride-catalyzed preparation of β-amino alcohols from epoxides. Synthesis 15:2298-2300. doi:10.1055/s-2003-41070 (Pubitemid 37409969)
30. Sabitha G, Reddy GSKK, Reddy KB, Reddy NM, Yadav JS (2005) Vanadium(III) chloride: a mild and efficient catalyst for the chemoselective deprotection of acetonides. J Mol Cat A 238:229-232. doi:10.1016/j.molcata.2005.05.028 (Pubitemid 41000345)
31. Wang XS, Li Q, Wu JR, Li YL, Yao CS, Tu SJ (2008) An efficient and highly selectivemethod for the synthesis of 3-arylbenzo-quinoline derivatives catalyzed by iodine via three-component reactions. Synthesis 12:1902-1910. doi:10.1055/s-2008-1067087 (Pubitemid 351934230)
32. Arend M, Westermann B, Risch N (1998) Modern variants of the Mannich reaction. Angew Chem Int Ed 37:10441070. doi:10.1002/(SICI)15213773(19980504)37: 8〈1044::AIDANIE1044〉3.0.CO;2-E
33. Kobayashi S, IshitaniH (1999) Catalytic enantio selective addition to imines. Chem Rev 99:1069-1094. doi:10.1021/cr980414z (Pubitemid 129588995)
34. Mannich C, Krosche W (1912) Ueber ein kondensations produkt aus formaldehyd, ammoniak und antipyrin. Arch Pharm 250: 647-667. doi:10.1002/ardp.19122500151
35. Marques MMB (2006) Catalytic enantioselective cross-Mannich reaction of aldehydes. Angew Chem Int Ed 45:348-352. doi:10.1002/anie.200502630
36. Bohme H, Haake M (1976) Iminium salts in organic chemistry. In: Taylor EC (ed) Advances in organic chemistry: methods and results. John Wiley and Sons, New York, p 107
37. Müller R, Goesmann H, Waldmann H (1999) N, N-Phthaloylamino acids as chiral auxiliaries in asymmetric Mannich-type reactions. Angew Chem Int Ed 38:184-187. doi:10.1002/(SICI)15213773(19990115)38:1/2〈184::AID- ANIE184〉3.0.CO;2-E (Pubitemid 29051219)
38. Du Y, Li Q, Xiong B, Hui X, Wang X, Feng Y, Meng T, Hu D, Zhang D, Wang M, Shen J (2010) Aromatic β-amino-ketone derivatives as novel selective non-steroidal progesterone receptor antagonists. BioorgMed Chem 18:4255-4268. doi:10.1016/j.bmc.2010.04.092
39. Lin Y, Huangshu L, Junhua Z, Xiujuan X (1991) The Mannich reaction between aromatic ketones, aromatic aldehydes and aromatic amines. Synthesis 9:717-718. doi:10.1055/s-1991-26554
40. Wu H, Shen Y, Fan L, Wan Y, Zhang P, Chen C, Wang W (2007) Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid. Tetrahedron 63:2404-2408. doi:10.1016/j.tet.2007.01.015 (Pubitemid 46204788)
41. Khan AT, Parvin T, Choudhury LH (2008) Bromodimethylsulfonium bromide catalyzed three-component Mannich-type reactions. Eur J Org Chem 834-839. doi:10.1002/ejoc.200700643
42. Ollevier T, Nadeau E (2004) Bismuth triflate-catalyzed three-component Mannich-type reaction. J Org Chem 69:9292-9295. doi:10.1021/jo048617c (Pubitemid 40004056)
43. Ollevier T, Nadeau E, Guay-Begin AA (2006) Direct-type catalytic three-component Mannich reaction in aqueous media. Tetrahedron Lett 47:8351-8354. doi:10.1016/j.tetlet.2006.09.082 (Pubitemid 44573364)
44. Wang R, Li B, Huang T, Shi L, Lu X (2007) NbCl5-Catalyzed one-pot Mannich-type reaction: three component synthesis of β-amino carbonyl compounds. Tetrahedron Lett 48:2071-2073. doi:10.1016/j.tetlet.2007.01.142 (Pubitemid 46275873)
45. Ranu BC, Samanta S, Guchhait SK (2002) Zinc tetrafluoroborate catalyzed Mannich-type reaction of aldimines and silyl enol ethers in aqueous medium. Tetrahedron 58:983-988. doi:10.1016/S0040-4020(01)01177-2 (Pubitemid 34093844)
46. Azizi N, Torkiyan L, Saidi MR (2006) Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids. Org Lett 8:2079-2082. doi:10.1021/ol060498v (Pubitemid 43823615)
47. Yi W-B, Cai C (2006) Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media. J Fluorine Chem 127:1515-1521. doi:10.1016/j.jfluchem.2006.07.009
48. 2O under solvent-free conditions. Eur J Org Chem 5152-5157. doi:10.1002/ejoc.200600493
49. Li H, Zeng H, Shao H (2009) Bismuth(III) chloride-catalyzed onepot mannich reaction: three-component synthesis of β-amino carbonyl compounds. Tetrahedron Lett 50:6858-6860. doi:10.1016/j.tetlet.2009.09.131