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Volumn 9, Issue , 2013, Pages 1957-1968

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

Author keywords

Bohlmann Rahtz; Continuous flow processing; Ethynyl ketones; Flow chemistry; Hantzsch dihydropyridine synthesis; Heterocycles; Microwave synthesis; Multicomponent reactions; Pyridine synthesis

Indexed keywords


EID: 84885034279     PISSN: None     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.9.232     Document Type: Article
Times cited : (39)

References (74)
  • 9
  • 11
    • 84865478162 scopus 로고    scopus 로고
    • doi:10.1002/tcr.201100041
    • Ley, S. V. Chem. Rec. 2012, 12, 378-390. doi:10.1002/tcr.201100041
    • (2012) Chem. Rec. , vol.12 , pp. 378-390
    • Ley, S.V.1
  • 12
    • 80054032471 scopus 로고    scopus 로고
    • doi:10.1002/chem.201102065
    • Glasnov, T. N.; Kappe, C. O. Chem.-Eur. J. 2011, 17, 11956-11968. doi:10.1002/chem.201102065
    • (2011) Chem.-Eur. J. , vol.17 , pp. 11956-11968
    • Glasnov, T.N.1    Kappe, C.O.2
  • 16
    • 34447108082 scopus 로고    scopus 로고
    • Microwave-assisted synthesis under continuous-flow conditions
    • DOI 10.1002/marc.200600665
    • Glasnov, T. N.; Kappe, C. O. Macromol. Rapid Commun. 2007, 28, 395-410. doi:10.1002/marc.200600665 (Pubitemid 47264268)
    • (2007) Macromolecular Rapid Communications , vol.28 , Issue.4 , pp. 395-410
    • Glasnov, T.N.1    Kappe, C.O.2
  • 18
    • 20444412378 scopus 로고    scopus 로고
    • A microreactor for microwave-assisted capillary (continuous flow) organic synthesis
    • DOI 10.1021/ja0512069
    • Comer, E.; Organ, M. G. J. Am. Chem. Soc. 2005, 127, 8160-8167. doi:10.1021/ja0512069 (Pubitemid 40799672)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.22 , pp. 8160-8167
    • Comer, E.1    Organ, M.G.2
  • 19
    • 29144487196 scopus 로고    scopus 로고
    • A microcapillary system for simultaneous, parallel microwave-assisted synthesis
    • DOI 10.1002/chem.200500820
    • Comer, E.; Organ, M. G. Chem.-Eur. J. 2005, 11, 7223-7227. doi:10.1002/chem.200500820 (Pubitemid 41803121)
    • (2005) Chemistry - A European Journal , vol.11 , Issue.24 , pp. 7223-7227
    • Comer, E.1    Organ, M.G.2
  • 20
    • 33746216295 scopus 로고    scopus 로고
    • Catalysis in capillaries by Pd thin films using Microwave-Assisted Continuous-flow Organic Synthesis (MACOS)
    • DOI 10.1002/anie.200503600
    • Shore, G.; Morin, S.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 2761-2766. doi:10.1002/anie.200503600 (Pubitemid 44099101)
    • (2006) Angewandte Chemie - International Edition , vol.45 , Issue.17 , pp. 2761-2766
    • Shore, G.1    Morin, S.2    Organ, M.G.3
  • 21
    • 17744385778 scopus 로고    scopus 로고
    • Microwave-assisted Suzuki reactions in a continuous flow capillary reactor
    • DOI 10.1016/j.apcata.2004.05.042, PII S0926860X04005307
    • He, P.; Haswell, S. J.; Fletcher, P. D. I. Appl. Catal., A 2004, 274, 111-114. doi:10.1016/j.apcata.2004.05.042 (Pubitemid 40573481)
    • (2004) Applied Catalysis A: General , vol.274 , Issue.1-2 , pp. 111-114
    • He, P.1    Haswell, S.J.2    Fletcher, P.D.I.3
  • 23
    • 23144446713 scopus 로고    scopus 로고
    • Monolithic polymer/carrier materials: Versatile composites for fine chemical synthesis
    • DOI 10.1016/j.cattod.2005.06.046, PII S0920586105003329, 2nd International Conference on Structured Catalysts and Reactors ISOSCAR-2
    • Kunz, U.; Kirschning, A.; Wen, H.-L; Solodenko, W.; Cecilia, R.; Kappe, C. O.; Turek, T. Catal. Today 2005, 105, 318-324. doi:10.1016/j.cattod.2005.06. 046 (Pubitemid 41084259)
    • (2005) Catalysis Today , vol.105 , Issue.3-4 , pp. 318-324
    • Kunz, U.1    Kirschning, A.2    Wen, H.-L.3    Solodenko, W.4    Cecilia, R.5    Kappe, C.O.6    Turek, T.7
  • 25
    • 33744803711 scopus 로고    scopus 로고
    • Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations
    • DOI 10.1002/chem.200501400
    • Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. K. Chem.-Eur. J. 2006, 12, 4407-4416. doi:10.1002/chem.200501400 (Pubitemid 43829112)
    • (2006) Chemistry - A European Journal , vol.12 , Issue.16 , pp. 4407-4416
    • Baxendale, I.R.1    Griffiths-Jones, C.M.2    Ley, S.V.3    Tranmer, G.K.4
  • 27
    • 33645412119 scopus 로고    scopus 로고
    • Process intensification: Oxidation of benzyl alcohol using a continuous isothermal reactor under microwave irradiation
    • DOI 10.1039/b512732g
    • Jachuck, R. J. J.; Selvaraj, D. K.; Varma, R. S. Green Chem. 2006, 8, 29-33. doi:10.1039/b512732g (Pubitemid 43485021)
    • (2006) Green Chemistry , vol.8 , Issue.1 , pp. 29-33
    • Jachuck, R.J.J.1    Selvaraj, D.K.2    Varma, R.S.3
  • 28
    • 0034654217 scopus 로고    scopus 로고
    • Esterification of benzoic acid in microwave tubular flow reactor
    • DOI 10.1016/S1385-8947(99)00171-0, PII S1385894799001710
    • Pipus, G.; Plazl, I.; Koloini, T. Chem. Eng. J. 2000, 76, 239-245. doi:10.1016/S1385-8947(99)00171-0 (Pubitemid 30205862)
    • (2000) Chemical Engineering Journal , vol.76 , Issue.3 , pp. 239-245
    • Pipus, G.1    Plazl, I.2    Koloini, T.3
  • 32
    • 0034180026 scopus 로고    scopus 로고
    • doi:10.1002/(SICI)1521-4125(20 0005)23:5<429::AID-CEAT 429>3.0.C O;2-T
    • Esveld, E.; Chemat, F.; van Haveren, J. Chem. Eng. Technol. 2000, 23, 429-435. doi:10.1002/(SICI)1521-4125(200005)23:5<429::AID-CEAT429>3.0.C O;2-T
    • (2000) Chem. Eng. Technol. , vol.23 , pp. 429-435
    • Esveld, E.1    Chemat, F.2    Van Haveren, J.3
  • 33
    • 0001628652 scopus 로고    scopus 로고
    • 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and microwave-accelerated green chemistry in methylation of phenols, indoles, and benzimidazoles with dimethyl carbonate
    • DOI 10.1021/ol016949n
    • Shieh, W.-C; Dell, S.; Repič, O. Org. Lett. 2001, 3, 4279-4281. doi:10.1021/ol016949n (Pubitemid 33627265)
    • (2001) Organic Letters , vol.3 , Issue.26 , pp. 4279-4281
    • Shieh, W.-C.1    Dell, S.2    Repic, O.3
  • 34
    • 0037025725 scopus 로고    scopus 로고
    • Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate
    • DOI 10.1016/S0040-4039(02)01116-4, PII S0040403902011164
    • Shieh, W.-C; Dell, S.; Repič, O. Tetrahedron Lett. 2002, 43, 5607-5609. doi:10.1016/S0040-4039(02)01116-4 (Pubitemid 34786522)
    • (2002) Tetrahedron Letters , vol.43 , Issue.32 , pp. 5607-5609
    • Shieh, W.-C.1    Dell, S.2    Repic, O.3
  • 35
    • 0042158757 scopus 로고    scopus 로고
    • Accelerated benzylation reaction utilizing dibenzyl carbonate as an alkylating reagent
    • DOI 10.1016/S0040-4039(03)01711-8
    • Shieh, W.-C; Lozanov, M.; Repič, O. Tetrahedron Lett. 2003, 44, 6943-6945. doi:10.1016/S0040-4039(03)01711-8 (Pubitemid 36976613)
    • (2003) Tetrahedron Letters , vol.44 , Issue.36 , pp. 6943-6945
    • Shieh, W.-C.1    Lozanov, M.2    Repic, O.3
  • 36
    • 0347717653 scopus 로고    scopus 로고
    • A study of the synthesis of triazoles using microwave irradiation
    • DOI 10.1023/B:MODI.0000006801.27748.3b, Microwaves in Combinatorial and High-Throughput Synthesis
    • Savin, K. A.; Robertson, M.; Gernert, D.; Green, S.; Hembre, E. J.; Bishop, J. Mol. Diversity 2003, 7, 171-174. doi:10.1023/B:MODI.0000006801.27748. 3b (Pubitemid 38095153)
    • (2003) Molecular Diversity , vol.7 , Issue.2-4 , pp. 171-174
    • Savin, K.A.1    Robertson, M.2    Gernert, D.3    Green, S.4    Hembre, E.J.5    Bishop, J.6
  • 38
    • 23944509440 scopus 로고    scopus 로고
    • Automated batch scale-up of microwave-promoted Suzuki and Heck coupling reactions in water using ultra-low metal catalyst concentrations
    • DOI 10.1016/j.tet.2005.07.063, PII S0040402005012469
    • Arvela, R. K.; Leadbeater, N. E.; Collins, M. J., Jr. Tetrahedron 2005, 61, 9349-9355. doi:10.1016/j.tet.2005.07.063 (Pubitemid 41206495)
    • (2005) Tetrahedron , vol.61 , Issue.39 , pp. 9349-9355
    • Arvela, R.K.1    Leadbeater, N.E.2    Collins Jr., M.J.3
  • 39
    • 25144446828 scopus 로고    scopus 로고
    • Microwave-assisted organic synthesis: Scale-up of palladium-catalyzed aminations using single-mode and multi-mode microwave equipment
    • DOI 10.1016/j.tet.2005.07.105, PII S004040200501392X
    • Loones, K. T. J.; Maes, B. U. W.; Rombouts, G.; Hostyn, S.; Diels, G. Tetrahedron 2005, 61, 10338-10348. doi:10.1016/j.tet.2005.07.105 (Pubitemid 41345732)
    • (2005) Tetrahedron , vol.61 , Issue.43 , pp. 10338-10348
    • Loones, K.T.J.1    Maes, B.U.W.2    Rombouts, G.3    Hostyn, S.4    Diels, G.5
  • 48
    • 33947729953 scopus 로고    scopus 로고
    • Regioselective microwave-assisted synthesis of substituted pyrazoles from ethynyl ketones
    • DOI 10.1055/s-2007-970783
    • Bagley, M. C; Lubinu, M. C; Mason, C. Synlett 2007, 704-708. doi:10.1055/s-2007-970783 (Pubitemid 46506822)
    • (2007) Synlett , Issue.5 , pp. 704-708
    • Bagley, M.C.1    Lubinu, M.C.2    Mason, C.3
  • 49
    • 84981754261 scopus 로고
    • doi:10.1002/cber.19570901021
    • Bohlmann, F.; Rahtz, D. Chem. Ber. 1957, 90, 2265-2272. doi:10.1002/cber.19570901021
    • (1957) Chem. Ber. , vol.90 , pp. 2265-2272
    • Bohlmann, F.1    Rahtz, D.2
  • 50
    • 35348959557 scopus 로고    scopus 로고
    • The Bohlmann-Rahtz pyridine synthesis: From discovery to applications
    • DOI 10.1055/s-2007-986674
    • Bagley, M. C; Glover, C; Merritt, E. A. Synlett 2007, 2459-2482. doi:10.1055/s-2007-986674 (Pubitemid 47597146)
    • (2007) Synlett , Issue.16 , pp. 2459-2482
    • Bagley, M.C.1    Glover, C.2    Merritt, E.A.3
  • 53
    • 4644285613 scopus 로고    scopus 로고
    • Stereoselective synthesis of the γ-lactam hydrolysate of the thiopeptide cyclothiazomycin
    • DOI 10.1021/ol0485870
    • Bagley, M. C; Xiong, X. Org. Lett. 2004, 6, 3401-3404. doi:10.1021/ol0485870 (Pubitemid 39297346)
    • (2004) Organic Letters , vol.6 , Issue.19 , pp. 3401-3404
    • Bagley, M.C.1    Xiong, X.2
  • 54
    • 3142745109 scopus 로고    scopus 로고
    • A new mild method for the one-pot synthesis of pyridines
    • DOI 10.1016/j.tetlet.2004.06.061, PII S004040390401353X
    • Xiong, X.; Bagley, M. C; Chapaneri, K. Tetrahedron Lett. 2004, 45, 6121-6124. doi:10.1016/j.tetlet.2004.06.061 (Pubitemid 38925278)
    • (2004) Tetrahedron Letters , vol.45 , Issue.32 , pp. 6121-6124
    • Xiong, X.1    Bagley, M.C.2    Chapaneri, K.3
  • 58
    • 0037064517 scopus 로고    scopus 로고
    • A new one-step synthesis of pyridines under microwave-assisted conditions
    • DOI 10.1016/S0040-4039(02)01975-5, PII S0040403902019755
    • Bagley, M. C; Lunn, R.; Xiong, X. Tetrahedron Lett. 2002, 43, 8331-8334. doi:10.1016/S0040-4039(02)01975-5 (Pubitemid 35223366)
    • (2002) Tetrahedron Letters , vol.43 , Issue.46 , pp. 8331-8334
    • Bagley, M.C.1    Lunn, R.2    Xiong, X.3
  • 61
    • 84980116545 scopus 로고
    • doi:10.1002/cber.18810140214
    • Hantzsch, A. Ber. Dtsch. Chem. Ges. 1881, 14, 1637-1638. doi:10.1002/cber.18810140214
    • (1881) Ber. Dtsch. Chem. Ges. , vol.14 , pp. 1637-1638
    • Hantzsch, A.1
  • 62
    • 84965040591 scopus 로고
    • doi:10.1002/jlac.18822150102
    • Hantzsch, A. JustusLiebigs Ann. Chem. 1882, 215, 1-82. doi:10.1002/jlac.18822150102
    • (1882) JustusLiebigs Ann. Chem. , vol.215 , pp. 1-82
    • Hantzsch, A.1
  • 68
    • 0034904876 scopus 로고    scopus 로고
    • doi:10.1055/s-2001-16043
    • Öhberg, L; Westman, J. Synlett 2001, 1296-1298. doi:10.1055/s-2001- 16043
    • (2001) Synlett , pp. 1296-1298
    • Öhberg, L.1    Westman, J.2
  • 70
    • 33646260703 scopus 로고    scopus 로고
    • doi:10.1055/s-2006-926407
    • Bagley, M. C; Lubinu, M. C. Synthesis 2006, 1283-1288. doi:10.1055/s-2006-926407
    • (2006) Synthesis , pp. 1283-1288
    • Bagley, M.C.1    Lubinu, M.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.