ULTRASONIC-PROMOTED SYNTHESIS OF FUNCTIONALIZED TETRAHYDROPYRIDINES USING TRIFLATE

Year 2017, Volume: 3 Issue: 2, 107 - 122, 30.12.2017

Zuhal Turgut , Emel Pelit

https://izlik.org/JA39WW88FA

Abstract

An easy, and effective multicomponent synthesis of a
highly substituted tetrahydropyridines has been achieved by reaction of
different substituted aromatic aldehydes, β-ketoester (methyl acetoacetate),
and p-methoxyaniline, in the presence of ytterbium(III)
trifluoromethanesulfonate, Yb(OTf)₃, 
as an efficient catalyst under ultrasound irradiation. This method has
supplied a different approach for the synthesis of highly substituted
tetrahydropyridines in moderate to good yields.

Keywords

Heterocycles , tetrahydropyridine , triflate , ultrasound

ULTRASONIC-PROMOTED SYNTHESIS OF FUNCTIONALIZED TETRAHYDROPYRIDINES USING TRIFLATE

https://izlik.org/JA39WW88FA

Abstract

Yüksek derecede sübstitüe edilmiş
tetrahidropiridinler, iterbiyum(III)triflorometansülfonat Yb(OTf)₃ katalizörlüğünde,
farklı sübstitüe aromatik aldehitler, β-ketoester (metil asetoasetat) ve
p-metoksianilinin kolay ve etkili reaksiyonuyla ultrason ışıması altında elde
edilmiştir. Bu yöntem yüksek derecede sübstitüe edilmiş tetrahidropiridinlerin
iyi verimlerle sentezi için farklı bir yaklaşım sağlamıştır.

Keywords

Heterosiklikler , tetrahidropiridin , triflat , ultrason

References

• Shi, F., Tan, W., Zhu, R., Xing, G., Tu, S., Catalytic asymmetric five-component tandem reaction: Diastereo- and enantioselective synthesis of densely functionalized tetrahydropyridines with biological importance. Advanced Synthesis & Catalysis, 355, 1605-1622, 2013.
• Harichandran, G., Amalraj, S.D., Shanmugam, P., A facile and efficient solid supported, one-pot synthesis of functionalized piperidine derivatives catalyzed by amberlite IRA400-Cl resin/I2/KI via multicomponent reaction J. Heterocyclic Chem., 50, 539-543, 2013.
• Khaksar, S., Vahdat, S.M., Alipour, M., Cerium (IV) triflate-catalyzed domino annulations approaches to the synthesis of highly substituted piperidines. Comptes Rendus Chimie, 16, 1024-1028, 2013.
• Balijapalli, U., Munusamy, S., Sundaramoorthy, K.N., Iyer, S.K., Metal-free, one-pot, rapid synthesis of tetrahydropyridines using acetic acid as solvent and catalyst at room temperature. Synthetic Communications, 44, 943-953, 2014.
• Mishra, S., Ghosh, R., Efficient one-pot synthesis of functionalized piperidine scaffolds via ZrOCL2.8H2O catalyzed tandem reactions of aromatic aldehydes with amines and acetoacetic esters. Tetrahedron Letters, 52, 2857-2861, 2011.
• Debache, A., Ghalem, W., Boulcina, R., Belfaitah, A., Rhouati, S., Carboni, B., An efficient one-step synthesis of 1,4-dihydropyridines via a triphenylphosphine-catalyzed three-component Hantzsch reaction under mild conditions. Tetrahedron Letters, 50, 5248-5250, 2009.
• Misra, M., Pandey, S.K., Pandey, V.P., Pandey, J., Tripathi, R., Tripathi, R.P., Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials. Bioorganic and Medicinal Chemistry, 17, 625-633, 2009.
• Mounsey, R.B., Mustafa, S., Robinson, L., Ross, R.A., Riedel, G., Pertwee, R.G., Teismann, P., Increasing levels of the endocannabinoid 2-AG is neuroprotective in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine mouse model of Parkinson’s disease. Experimental Neurology, 273, 36-44 2015.
• Dai, B., Duan, Y., Liu, X., Song, L., Zhang, M., Cao, W., Zhu, S., Deng, H., Shao, M., Iodine catalyzed one-pot multi-component reaction to CF3-containing spiro[indene-2,3’-piperidine] derivatives. Journal of Fluorine Chemistry, 133, 127-133, 2012.
• Khan, A.T., Khan, M., Bannuru, K.K.R., Iodine catalyzed one-pot five-component reactions for direct synthesis of densely functionalized piperidines. Tetrahedron, 66, 7762-7772, 2010.
• Umamahesh, B., Sathesh. V., Ramachandran, G., Sathishkumar, M., Sathiyanarayanan, K., LaCl3.7H2O as an efficient catalyst for one-pot synthesis of highly functionalized piperidines via multi-component organic reactions. Catalysis Letters. 142, 895-900, 2012.
• Sarkate, A.P., Sangshetti, J.N., Dharbale, N.B., Sarkate, A.P., Shinde, D.B., Sulfamic acid catalyzed five component reaction for efficient and one-pot synthesis of densely functionalized tetrahydropyridine scaffold. Journal of the Chilean Chemical Society, 60, No1, 2832-2836, 2015.
• Sajadikhah, S.S., Maghsoodlou, M.T., Hazeri, N., Habibi-Khorassani, S.M., Willis, A.C., One-pot five-component synthesis of hihly functionalized piperidines using oxalic acid dehydrate as a homogeneous catalyst. Chinese Chemical Letters, 23, 569-572, 2012.
• Wang, H., Mo, L., Zhang, Z., Cerium ammonium nitrate-catalyzed multicomponent reaction for efficient synthesis of functionalized tetrahydropyridines. ACS Combinatorial Science, 13, 181-185, 2011.
• Sajadikhah, S.S., Maghsoodlou, M.T., Hazeri, N., Habibi-Khorassani, S.M., Shams-Najafi, S.J., One-pot multicomponent synthesis of highly substituted piperidines using p-toluenesulfonic acid monohydrate as catalyst. Monatsh. Chem., 143, 939-945, 2012.
• Khan, A.T., Lal, M., Khan, M., Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB). Tetrahedron Letters, 51, 4419-4424, 2010.
• Chouguiat, L., Boulcina, R., Debache, A., Bi(OTf)3 as a powerful and efficient catalyst for the synthesis of highly functionalized piperidines. Journal of Chemical and Pharmaceutical Research, 6 (6), 79-85, 2014.
• Prajapti, S.K., Nagarsenkar, A., Gaggilapu S.D., Babu B.N., B(C6F5)3 as versatile catalyst: an efficient and mild protocol for the one-pot synthesis of functionalized piperidines and 2-substituted benzimidazole derivatives. Tetrahedron Letters, 56, 6795-6799, 2015.
• Verma, S., Jain, S.L., Sain, B., PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines. Beilstein Journal of Organic Chemistry, 7, 1334-1341, 2011.
• Aeluri, R., Ganji, R.J., Marapaka, A.K., Pillalamarri, V., Alla, M., Addlagatta, A., Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of huma puromycin sensitive. European Journal of Medicinal Chemistry, 106, 26-33, 2015.
• Kobayashi, S., Sugira, M., Kitagawa, H., Lam, W.L., Rare-earth metal triflates in organic synthesis. Chemical Reviews, 102, 2227-2302, 2002.
• Pelit, E., Turgut, Z. Three-component aza-Diels-Alder reactions using Yb(OTf)3 catalyst under conventional/ultrasonic techniques. Ultrasonics Sonochemistry, 21 (4), 1600-1607, 2014.
• Ozturkcan, S.A., Turhan, K., Turgut, Z., Karadayi, M., Gulluce, M., Ultrasonic synthesis, characterization of B-aminoketones by bismuth(III)triflate and determination of antigenotoxic properties. Toxicology and Industrial Health, 31(10), 911-919, 2015.
• Shabalala, N.G., Pagadala, R., Jonnalagadda, S.B., Ultrasonic-accelerated rapid protocol for the improved synthesis of pyrazoles. Ultrasonics Sonochemistry, 27, 423-429, 2015.
• Javidan, A., Ziarati, A., Safaei-Ghomi, J., Simultaneous sonication assistance for the synthesis of tetrahydropyridines and its efficient catalyst ZrP2O7 nanoparticles. Ultrasonics Sonochemistry, 21, 1150-1154, 2014.
• Brahmachari, G., Das, S., Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature. Tetrahedron Letters, 53, 1479-1484, 2012.
• Zhou, Q., Wan, Y., Zhang, X., Zhang, L., Zou, H., Cui H., Zhou S., Wang, H., Wu H., The first example of glucose-containing carbene Bronsted acid synthesis and catalysis: efficient synthesis of five substituted tetrahydropyridines. Tetrahedron, 71, 7070-7072, 2015.
• Eshghi, H., Khojastehnezhad, A., Moeinpour, F., Rezaeian, S., Bakavoli, M., Teymouri, M., Rostami, A., Haghbeen, K., Nanomagnetic organic-inorganic hybrid (Fe@Si-Gu-Prs): a novel magnetically green catalyst for the synthesis of tetrahydropyridine derivatives at room temperature under solvent-free conditions. Tetrahedron, 71, 436-444, 2015.
• Clarke, P.A., Zaytsev, A.V., Whitwood, A.C., Pot, Atom, and step economic (PASE) synthesis of highly substituted piperidines: A five-component condensation. Synthesis, 3530-3532, 2008.