10.23 Product Class 23: Pyrido[X,Y-b ]indoles (Carbolines)
Book
Editors: Joule, J. A.; Murai, T.
Title: Knowledge Updates 2018/2
Print ISBN: 9783132423176; Online ISBN: 9783132423206; Book DOI: 10.1055/b-006-160285
1st edition © 2018 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
Methods for the synthesis of the four isomeric carboline (pyrido[X,Y-b]indole) ring systems are discussed. Reports from 1919, when the word “carboline” was first coined, up to 2015 are covered, with some references from early 2016 also included.
Key words
carbolines - 9H-pyrido[2,3-b]indoles - 9H-pyrido[3,4-b]indoles - 5H-pyrido[4,3-b]indoles - 5H-pyrido[3,2-b]indoles - indoles - pyridines - carbon–carbon bond formation - carbon–nitrogen bond formation - palladium catalysis - aromatization - dehydrogenation - tryptamines- 10 Rook Y, Schmidtke K.-U, Gaube F, Schepmann D, Wünsch B, Heilmann J, Lehmann J, Winckler T. J. Med. Chem. 2010; 53: 3611
- 11 Blom JF, Brütsch T, Barbaras D, Bethuel Y, Locher HH, Hubschwerlen C, Gademann K. Org. Lett. 2006; 8: 737
- 12 Zhang G, Cao R, Guo L, Ma Q, Fan W, Chen X, Li J, Shao G, Qiu L, Ren Z. Eur. J. Med. Chem. 2013; 65: 21
- 14 Angulo G, Carmona C, Pappalardo RR, Muñoz MA, Guardado P, Marcos ES, Balón M. J. Org. Chem. 1997; 62: 5104
- 16 Albert A, In: Physical Methods in Heterocyclic Chemistry Katritzky AR. Academic Press New York 1963; 3.
- 20 Van Baelen G, Hostyn S, Dhooghe L, Tapolcsányi P, Mátyus P, Lemière G, Dommisse R, Kaiser M, Brun R, Cos P, Maes L, Hajós G, Riedl Z, Nagy I, Maes BUW, Pieters L. Bioorg. Med. Chem. 2009; 17: 7209
- 21 Arzel E, Rocca P, Grellier P, Labaeïd M, Frappier F, Guéritte F, Gaspard C, Marsais F, Godard A, Quéguiner G. J. Med. Chem. 2001; 44: 949
- 32 Marion L, In: The Alkaloids: Chemistry and Physiology Manske RHF, Holmes HL. Academic New York 1952; 2. 369
- 33 Schlittler E, In: The Alkaloids: Chemistry and Physiology Manske RHF. Academic New York 1965; 8. 287
- 34 Manske RHF, In: The Alkaloids: Chemistry and Physiology Manske RHF. Academic New York 1965; 8. 693
- 35 Szántay C, Blaskó G, Honty K, Dörnyei G, In: The Alkaloids: Chemistry and Pharmacology Brossi A. Academic New York 1986; 27. 131
- 36 Monteiro HJ, In: The Alkaloids: Chemistry and Physiology Manske RHF. Academic New York 1968; 11. 145
- 37 Husson H.-P, In: The Alkaloids: Chemistry and Pharmacology Brossi A. Academic New York 1985; 26. 1
- 39 Manske RHF, In: The Alkaloids: Chemistry and Physiology Manske RHF. Academic New York 1965; 8. 47
- 44 Ohmoto T, Koike K, In: The Alkaloids: Chemistry and Pharmacology Brossi A. Academic San Diego 1989; 36. 135
- 45 Dvoráčková S, Sedmera P, Potěšilová H, Šantavy F, Šimánek V. Collect. Czech. Chem. Commun. 1984; 49: 1536
- 47 Grellier P, Ramiaramanana L, Millerioux V, Deharo E, Schrével J, Frappier F, Trigalo F, Bodo B, Pousset J.-L. Phytother. Res. 1996; 10: 317
- 54 Takeuchi T, Oishi S, Watanabe T, Ohno H, Sawada J.-i, Matsuno K, Asai A, Asada N, Kitaura K, Fujii N. J. Med. Chem. 2011; 54: 4839
- 56 Schmittel M, Steffen J.-P, Rodríguez D, Engelen B, Neumann E, Cinar ME. J. Org. Chem. 2008; 73: 3005
- 59 Tahri A, Buysens KJ, Van der Eycken EV, Vandenberghe DM, Hoornaert GJ. Tetrahedron 1998; 54: 13 211
- 74 Mineno M, Sera M, Ueda T, Mizufune H, Zanka A, O’Bryan C, Brown J, Scorah N. J. Org. Chem. 2015; 80: 1564
- 76 Das S, Harde RL, Shelke DE, Khairatkar-Joshi N, Bajpai M, Sapalya RS, Surve HV, Gudi GS, Pattem R, Behera DB, Jadhav SB, Thomas A. Bioorg. Med. Chem. Lett. 2014; 24: 2073
- 100 Sharma SK, Gupta S, Saifuddin M, Mandadapu AK, Agarwal PK, Gauniyal HM, Kundu B. Tetrahedron Lett. 2011; 52: 65
- 110 Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B. Bioorg. Med. Chem. 2007; 15: 5615
- 113 Lin Y.-C, Chen Y.-F, Tseng L.-S, Lee Y.-H, Morris-Natschke SL, Kuo S.-C, Yang N.-S, Lee K.-H, Huang L.-J. Eur. J. Med. Chem. 2016; 110: 98
- 114 Mahmoud KA, Krug M, Wersig T, Slynko I, Schächtele C, Totzke F, Sippl W, Hilgeroth A. Bioorg. Med. Chem. Lett. 2014; 24: 1948
- 116 Mahmoud KA, Wersig T, Slynko I, Totzke F, Schächtele C, Oelze M, Sippl W, Ritter C, Hilgeroth A. MedChemComm 2014; 5: 659
- 124 Suschitzky H, Wakefield BJ, Walocha K, Hughes N, Nelson AJ. J. Chem. Soc., Perkin Trans. 1 1983; 637
- 127 Peng Y.-H, Ueng S.-H, Tseng C.-T, Hung M.-S, Song J.-S, Wu J.-S, Liao F.-Y, Fan Y.-S, Wu M.-H, Hsiao W.-C, Hsueh C.-C, Lin S.-Y, Cheng C.-Y, Tu C.-H, Lee L.-C, Cheng M.-F, Shia K.-S, Shih C, Wu S.-Y. J. Med. Chem. 2016; 59: 282
- 128 Wang Y, Wu Z, Guida BF, Lawrence SK, Neeb MJ, Rivero RA, Douglas SA, Jin J. Bioorg. Med. Chem. Lett. 2008; 18: 4936
- 129 Son YH, Kim YJ, Park MJ, Oh H.-Y, Park JS, Yang JH, Suh MC, Kwon JH. J. Mater. Chem. C 2013; 1: 5008
- 134 Cho MJ, Kim SJ, Yoon SH, Shin J, Hong TR, Kim HJ, Son YH, Kang JS, Um HA, Lee TW, Bin J.-K, Lee BS, Yang JH, Chae GS, Kwon JH, Choi DH. ACS Appl. Mater. Interfaces 2014; 6: 19 808
- 147 Krug M, Wichapong K, Erlenkamp G, Sippl W, Schächtele C, Totzke F, Hilgeroth A. ChemMedChem 2011; 6: 63
- 148 Panunzio M, Tamanini E, St-Denis Y, Sabbatini FM, Di Fabio R, Xia Z. Synth. Commun. 2007; 37: 4239
- 154 Kadiyala RR, Tilly D, Nagaradja E, Roisnel T, Matulis VE, Ivashkevich OA, Halauko YS, Chevallier F, Gros PC, Mongin F. Chem.–Eur. J. 2013; 19: 7944
- 156 Tagawa S, Choshi T, Okamoto A, Nishiyama T, Watanabe S, Hatae N, Hibino S. Heterocycles 2013; 87: 357
- 170 Namjoshi OA, Gryboski A, Fonseca GO, VanLinn ML, Wang Z.-j, Deschamps JR, Cook JM. J. Org. Chem. 2011; 76: 4721
- 188 Drung B, Scholz C, Barbosa VA, Nazari A, Sarragiotto MH, Schmidt B. Bioorg. Med. Chem. Lett. 2014; 24: 4854
- 191 Zheng C, Fang Y, Tong W, Li G, Wu H, Zhou W, Lin Q, Yang F, Yang Z, Wang P, Peng Y, Pang X, Yi Z, Luo J, Liu M, Chen Y. J. Med. Chem. 2014; 57: 600
- 194 Behforouz M, Cai W, Stocksdale MG, Lucas JS, Jung JY, Briere D, Wang A, Katen KS, Behforouz NC. J. Med. Chem. 2003; 46: 5773
- 195 Seradj H, Cai W, Erasga NO, Chenault DV, Knuckles KA, Ragains JR, Behforouz M. Org. Lett. 2004; 6: 473
- 196 Hassani M, Cai W, Holley DC, Lineswala JP, Maharjan BR, Ebrahimian GR, Seradj H, Stocksdale MG, Mohammadi F, Marvin CC, Gerdes JM, Beall HD, Behforouz M. J. Med. Chem. 2005; 48: 7733
- 197 Cai W, Hassani M, Karki R, Walter ED, Koelsch KH, Seradj H, Lineswala JP, Mirzaei H, York JS, Olang F, Sedighi M, Lucas JS, Eads TJ, Rose AS, Charkhzarrin S, Hermann NG, Beall HD, Behforouz M. Bioorg. Med. Chem. 2010; 18: 1899
- 201 Zhang P, Sun X, Xu B, Bijian K, Wan S, Li G, Alaoui-Jamali M, Jiang T. Eur. J. Med. Chem. 2011; 46: 6089
- 203 Yang M.-L, Kuo P.-C, Hwang T.-L, Chiou W.-F, Qian K, Lai C.-Y, Lee K.-H, Wu T.-S. Bioorg. Med. Chem. 2011; 19: 1674
- 204 Manda S, Sharma S, Wani A, Joshi P, Kumar V, Guru SK, Bharate SS, Bhushan S, Vishwakarma RA, Kumar A, Bharate SB. Eur. J. Med. Chem. 2016; 107: 1
- 219 Lindsley CW, Bogusky MJ, Leister WH, McClain RT, Robinson RG, Barnett SF, Defeo-Jones D, Ross III CW, Hartman GD. Tetrahedron Lett. 2005; 46: 2779
- 233 Ábrányi-Balogh P, Földesi T, Grün A, Volk B, Keglevich G, Milen M. Tetrahedron Lett. 2016; 57: 1953
- 240 La Regina G, Famiglini V, Passacantilli S, Pelliccia S, Punzi P, Silvestri R. Synthesis 2014; 46: 2093
- 248 Desroses M, Koolmeister T, Jacques S, Llona-Minguez S, Jacques-Cordonnier M.-C, Cázares-Körner A, Helleday T, Scobie M. Tetrahedron Lett. 2013; 54: 3554
- 250 Ghislieri D, Green AP, Pontini M, Willies SC, Rowles I, Frank A, Grogan G, Turner NJ. J. Am. Chem. Soc. 2013; 135: 10 863
- 255 Bartoli G, Bosco M, Giuli S, Giuliani A, Lucarelli L, Marcantoni E, Sambri L, Torregiani E. J. Org. Chem. 2005; 70: 1941
- 256 Shankaraiah N, Siraj KP, Nekkanti S, Srinivasulu V, Sharma P, Senwar KR, Sathish M, Vishnuvardhan MVPS, Ramakrishna S, Jadala C, Nagesh N, Kamal A. Bioorg. Chem. 2015; 59: 130
- 257 Shankaraiah N, Jadala C, Nekkanti S, Senwar KR, Nagesh N, Shrivastava S, Naidu VGM, Sathish M, Kamal A. Bioorg. Chem. 2016; 64: 42
- 261 Xin B, Tang W, Wang Y, Lin G, Liu H, Jiao Y, Zhu Y, Yuan H, Chen Y, Lu T. Bioorg. Med. Chem. Lett. 2012; 22: 4783
- 265 Devi N, Singh D, Honey , Mor S, Chaudhary S, Rawal RK, Kumar V, Chowdhurya AK, Singh V. RSC Adv. 2016; 6: 43 881
- 273 Ikeda R, Iwaki T, Iida T, Okabayashi T, Nishi E, Kurosawa M, Sakai N, Konakahara T. Eur. J. Med. Chem. 2011; 46: 636
- 275 Laronze M, Boisbrun M, Léonce S, Pfeiffer B, Renard P, Lozach O, Meijer L, Lansiaux A, Bailly C, Sapi J, Laronze J.-Y. Bioorg. Med. Chem. 2005; 13: 2263
- 284 Kamal A, Tangella Y, Manasa KL, Sathish M, Srinivasulu V, Chetna J, Alarifi A. Org. Biomol. Chem. 2015; 13: 8652
- 285 Bremner JB, Sengpracha W, Southwell I, Bourke C, Skelton BW, White AH. Aust. J. Chem. 2004; 57: 273
- 289 Dai J.-K, Dan W.-J, Li N, Du H.-T, Zhang J.-W, Wang J.-R. Bioorg. Med. Chem. Lett. 2016; 26: 580
- 291 Brahmbhatt KG, Ahmed N, Sabde S, Mitra D, Singh IP, Bhutani KK. Bioorg. Med. Chem. Lett. 2010; 20: 4416
- 295 García MD, Wilson AJ, Emmerson DPG, Jenkins PR, Mahale S, Chaudhuri B. Org. Biomol. Chem. 2006; 4: 4478
- 302 Thompson MJ, Louth JC, Little SM, Jackson MP, Boursereau Y, Chen B, Coldham I. ChemMedChem 2012; 7: 578
- 303 Castro AC, Dang LC, Soucy F, Grenier L, Mazdiyasni H, Hottelet M, Parent L, Pien C, Palombella V, Adams J. Bioorg. Med. Chem. Lett. 2003; 13: 2419
- 307 Suzuki H, Unemoto M, Hagiwara M, Ohyama T, Yokoyama Y, Murakami Y. J. Chem. Soc., Perkin Trans. 1 1999; 1717
- 308 Murakami Y, Yokoyama Y, Aoki C, Suzuki H, Sakurai K, Shinohara T, Miyagi C, Kimura Y, Takahashi T, Watanabe T, Ohmoto T. Chem. Pharm. Bull. 1991; 39: 2189
- 309 Suzuki H, Iwata C, Sakurai K, Tokumoto K, Takahashi H, Hanada M, Yokoyama Y, Murakami Y. Tetrahedron 1997; 53: 1593
- 310 Suzuki H, Tsukakoshi Y, Tachikawa T, Miura Y, Adachi M, Murakami Y. Tetrahedron Lett. 2005; 46: 3831
- 318 Watanabe T, Kobayashi A, Nioshiura M, Takahashi H, Usui T, Kamiyama I, Mochizuki N, Noritake K, Yokoyama Y, Murakami Y. Chem. Pharm. Bull. 1991; 39: 1152
- 323 Cuny GD, Ulyanova NP, Patnaik D, Liu J.-F, Lin X, Auerbach K, Ray SS, Xian J, Glicksman MA, Stein RL, Higgins JMG. Bioorg. Med. Chem. Lett. 2012; 22: 2015
- 325 Meinguet M, Bruyère C, Frédérick R, Mathieu V, Vancraeynest C, Pochet L, Laloy J, Mortier J, Wolber G, Kiss R, Masereel B, Wouters J. Eur. J. Med. Chem. 2015; 94: 45
- 326 Shi B, Cao R, Fan W, Guo L, Ma Q, Chen X, Zhang G, Qin L, Song H. Eur. J. Med. Chem. 2013; 60: 10
- 327 Murakami Y, Imai N, Miura T, Sugimura T, Wakabayashi K, Totsuka Y, Hada N, Yokoyama Y, Suzuki H, Mitsunaga K. Heterocycles 2010; 80: 455
- 328 Allen MS, Tan Y.-C, Trudell ML, Narayanan K, Schindler LR, Martin MJ, Schultz C, Hagen TJ, Koehler KF, Codding PW, Skolnick P, Cook JM. J. Med. Chem. 1990; 33: 2343
- 330 Markgraf JH, Dowst AA, Hensley LA, Jakobsche CE, Kaltner CJ, Webb PJ, Zimmerman PW. Tetrahedron 2005; 61: 9102
- 331 Itoh T, Miyazaki M, Ikeda S, Nagata K, Yokoya M, Matsuya Y, Enomoto Y, Ohsawa A. Tetrahedron 2003; 59: 3527
- 335 Bonazzi S, Barbaras D, Patiny L, Scopelliti R, Schneider P, Cole ST, Kaiser M, Brun R, Gademann K. Bioorg. Med. Chem. 2010; 18: 1464
- 336 Ma C, Cao R, Shi B, Li S, Chen Z, Yi W, Peng W, Ren Z, Song H. Eur. J. Med. Chem. 2010; 45: 1515
- 338 Rao TSC, Saha S, Raolji GB, Patro B, Risbood P, Difilippantonio MJ, Tomaszewski JE, Malhotra SV. Tetrahedron Lett. 2013; 54: 487
- 341 Otto R, Penzis R, Gaube F, Adolph O, Föhr KJ, Warncke P, Robaa D, Appenroth D, Fleck C, Enzensperger C, Lehmann J, Winckler T. J. Med. Chem. 2015; 58: 6710
- 347 Kardono LBS, Angerhofer CK, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD. J. Nat. Prod. 1991; 54: 1360
- 352 Wang Y, Jin Q, Lin G, Yang T, Wang Z, Lu Y, Tang Y, Liu L, Lu T. Chem. Pharm. Bull. 2012; 60: 435
- 355 Lunagariya NA, Gohil VM, Kushwah V, Neelagiri S, Jain S, Singh S, Bhutani KK. Bioorg. Med. Chem. Lett. 2016; 26: 789
- 386 Reniers J, Robert S, Frederick R, Masereel B, Vincent S, Wouters J. Bioorg. Med. Chem. 2011; 19: 134
- 388 Cao R, Fan W, Guo L, Ma Q, Zhang G, Li J, Chen X, Ren Z, Qiu L. Eur. J. Med. Chem. 2013; 60: 135
- 389 Dodd RH, Ouannès C, de Carvalho LP, Valin A, Venault P, Chapouthier G, Rossier J, Potier P. J. Med. Chem. 1985; 28: 824
- 393 Allen MS, LaLoggia AJ, Dorn LJ, Martin MJ, Costantino G, Hagen TJ, Koehler KF, Skolnick P, Cook JM. J. Med. Chem. 1992; 35: 4001
- 396 Cao R, Yi W, Wu Q, Guan X, Feng M, Ma C, Chen Z, Song H, Peng W. Bioorg. Med. Chem. Lett. 2008; 18: 6558
- 400 Kamal A, Sathish M, Nayak VL, Srinivasulu V, Kavitha B, Tangella Y, Thummuri D, Bagul C, Shankaraiah N, Nagesh N. Bioorg. Med. Chem. 2015; 23: 5511
- 403 Takasu K, Shimogama T, Saiin C, Kim H, Wataya Y, Ihara M. Bioorg. Med. Chem. Lett. 2004; 14: 1689
- 404 Takasu K, Shimogama T, Sain C, Kim H.-S, Wataya Y, Brun R, Ihara M. Chem. Pharm. Bull. 2005; 53: 653
- 405 Liu L, Yang Q, Yu H, Li J.-L, Pei Y.-N, Zhu H.-J, Li Z.-Q, Wang X.-K. Tetrahedron 2015; 71: 3296
- 408 Bolognesi ML, Tran HNA, Staderini M, Monaco A, López-Cobeñas A, Bongarzone S, Biarnés X, López-Alvarado P, Cabezas N, Caramelli M, Carloni P, Menéndez JC, Legname J. ChemMedChem 2010; 5: 1324
- 409 Chen Z, Cao R, Yu L, Shi B, Sun J, Guo L, Ma Q, Yi W, Song X, Song H. Eur. J. Med. Chem. 2010; 45: 4740
- 410 Kamal A, Rao MPN, Swapna P, Srinivasulu V, Bagul C, Shaik AB, Mullagiri K, Kovvuri J, Reddy VS, Vidyasagar K, Nagesh N. Org. Biomol. Chem. 2014; 12: 2370
- 411 Kamal A, Srinivasulu V, Nayak VL, Sathish M, Shankaraiah N, Bagul C, Reddy NVS, Rangaraj N, Nagesh N. ChemMedChem 2014; 9: 2084
- 412 Chauhan SS, Singh AK, Meena S, Lohani M, Singh A, Arya RK, Cheruvu SH, Sarkar J, Gayen JR, Datta D, Chauhan PMS. Bioorg. Med. Chem. Lett. 2014; 24: 2820
- 416 Baiget J, Llona-Minguez S, Lang S, MacKay SP, Suckling CJ, Sutcliffe OB. Beilstein J. Org. Chem. 2011; 7: 1407
- 423 Ling Y, Xu C, Luo L, Cao J, Feng J, Xue Y, Zhu Q, Ju C, Li F, Zhang Y, Zhang Y, Ling X. J. Med. Chem. 2015; 58: 9214
- 427 Ashok P, Chander S, Balzarini J, Pannecouque C, Murugesan S. Bioorg. Med. Chem. Lett. 2015; 25: 1232
- 430 Yin W, Majumder S, Clayton T, Petrou S, VanLinn ML, Namjoshi OA, Ma C, Cromer BA, Roth BL, Platt DM, Cook JM. Bioorg. Med. Chem. 2010; 18: 7548
- 431 Ikeda R, Kimura T, Tsutsumi T, Tamura S, Sakai N, Konakahara T. Bioorg. Med. Chem. Lett. 2012; 22: 3506
- 436 Bratt J, Iddon B, Mack AG, Suschitzky H, Taylor JA, Wakefield BJ. J. Chem. Soc., Perkin Trans. 1 1980; 648
- 437 Aoyama H, Sako K, Sato S, Nakamura M, Miyachi H, Goto Y, Okamoto M, Baba M, Hashimoto Y. Heterocycles 2009; 77: 779
- 447 Clark RD, Miller AB, Berger J, Repke DB, Weinhardt KK, Kowalczyk BA, Eglen RM, Bonhaus DW, Lee C.-H, Michel AD, Smith WL, Wong EHF. J. Med. Chem. 1993; 36: 2645
- 462 Oliveira-Campos AMF, Gonçalves JCO, Rodrigues LM, Esteves AP. 14th International Electronic Conference on Organic Synthesis (ECSOC-14) 2010; paper C003; available online at http://www.usc.es/congresos/ecsoc/14/
- 466 Molina A, Vaquero JJ, Garcia-Navio JL, Alvarez-Builla J, de Pascual-Teresa B, Gago F, Rodrigo MM, Ballesteros M. J. Org. Chem. 1996; 61: 5587
- 474 Fedorovskiy OYu, Gusev DV, Chkanikov ND, Ivanov AV, Scherbakova VS. Fluorine Notes 2014; 2: available online at http://notes.fluorine1.ru/public/2014/2_2014/letters/index.html
- 475 Butin AV, Pilipenko AS, Milich AA, Finko AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 613
- 478 Akué-Gédu R, Couturier D, Hénichart J.-P, Rigo B, Sanz G, Van Hijfte L, Bourry A. Tetrahedron 2012; 68: 5644
- 479 Chen J, Liu T, Wu R, Lou J, Cao J, Dong X, Yang B, He Q, Hu Y. Bioorg. Med. Chem. 2010; 18: 8478
- 483 Ran X, Zhao Y, Liu L, Bai L, Yang C.-Y, Zhou B, Meagher JL, Chinnaswamy K, Stuckey JA, Wang S. J. Med. Chem. 2015; 58: 4927
- 484 Chen J, Dong X, Liu T, Lou J, Jiang C, Huang W, He Q, Yang B, Hu Y. Bioorg. Med. Chem. 2009; 17: 3324
- 488 Neue B, Reiermann R, Gerdes K, Fröhlich R, Wibbeling B, Würthwein E.-U. J. Org. Chem. 2011; 76: 8794
- 490 Rocca P, Cochennec C, Marsais F, Thomas-dit-Dumont L, Mallet M, Godard A, Quéguiner G. J. Org. Chem. 1993; 58: 7832
- 496 Mazu TK, Etukala JR, Jacob MR, Khan SI, Walker LA, Ablordeppey SY. Eur. J. Med. Chem. 2011; 46: 2378
- 499 Franck P, Hostyn S, Dajka-Halász B, Polonka-Bálint A, Monsieurs K, Mátyus P, Maes BUW. Tetrahedron 2008; 64: 6030
- 500 Zhao J, Li P, Wu C, Chen H, Ai W, Sun R, Ren H, Larock RC, Shi F. Org. Biomol. Chem. 2012; 10: 1922
- 501 Trofimov BA, Schmidt EYu, Mikhaleva AI, Zorina NV, Ushakov IA, Afonin AV, Vasil’tsov AM. Mendeleev Commun. 2007; 17: 40
- 502 Sharma SK, Mandadapu AK, Saifuddin M, Gupta S, Agarwal PK, Mandwal AK, Gauniyal HM, Kundu B. Tetrahedron Lett. 2010; 51: 6022