Synthesis 2022; 54(10): 2516-2526
DOI: 10.1055/a-1736-4200
paper

Towards Rare-Functionalized N-Alkenyl-1H-pyrroles via Regioselectively Metalated N-Isopropenyl-1H-pyrroles

Ol'ga A. Tarasova
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Marina A. Maximova
b   Department of Industrial Ecology and Life Safety, Irkutsk National Research Technical University, 83 Lermontov Str., 664074 Irkutsk, Russian Federation
,
Alexander I. Albanov
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Nina A. Nedolya
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Boris A. Trofimov
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
› Author Affiliations


Abstract

Deprotonative metalation of N-isopropenyl-1H-pyrroles with superbases followed by trapping with a variety of electrophiles was studied as an effective tool for the regioselective functionalization of 1H-pyrroles.

Supporting Information



Publication History

Received: 18 November 2021

Accepted after revision: 11 January 2022

Accepted Manuscript online:
11 January 2022

Article published online:
01 March 2022

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  • References

    • 1a Schofield K. Hetero-Aromatic Nitrogen Compounds: Pyrroles and Pyridines. Springer; New York: 1967
    • 1b d’Ischia M, Napolitano A, Pezzella A. Pyrroles and Their Benzo Derivatives: Applications. In Comprehensive Heterocyclic Chemistry III, Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 353
    • 1c Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
    • 1d Walsh CT, Garneau-Tsodikova S, Howard-Jones AR. Nat. Prod. Rep. 2006; 23: 517
    • 1e Black DStC. 1H-Pyrroles. In Science of Synthesis, Vol. 9. Maas G. Georg Thieme Verlag; Stuttgart: 2001: 441
    • 1f Gribble GW. Pyrroles and Their Benzo Derivatives: Applications. In Comprehensive Heterocyclic Chemistry, Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996: 207
    • 1g McNab H, Monahan LC. Pyrroles: The Synthesis, Reactivity and Physical Properties of Substituted Pyrroles. In The Chemistry of Heterocyclic Compounds, Part 2, Vol. 48. Jones RA. John Wiley & Sons; New York: 1992: 547
    • 1h Sunderberg RJ. Pyrroles and Their Benzo Derivatives: Synthesis and Applications. In Comprehensive Heterocyclic Chemistry, Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 313
    • 2a Kalinin AA, Mamedov VA. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2011; 46: 1423
    • 2b Trofimov BA, Nedolya NA. Pyrroles and Their Benzo Derivatives: Reactivity. In Comprehensive Heterocyclic Chemistry III, Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 45
    • 2c Saracoglu N. Top. Heterocycl. Chem. 2007; 11: 1
    • 2d Banwell MG, Goodwin TE, Ng S, Smith JA, Wong DJ. Eur. J. Org. Chem. 2006; 3043
    • 2e Abele E, Abele R, Lukevic E. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2004; 40: 1
    • 2f Black DStC. Pyrroles and Their Benzo Derivatives: Reactivity. In Comprehensive Heterocyclic Chemistry, Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1996: 39
    • 2g Jones RA. Pyrroles and Their Benzo Derivatives: Reactivity. In Comprehensive Heterocyclic Chemistry, Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 201
    • 3a Khajuria R, Dham S, Kapoor KK. RSC Adv. 2016; 6: 37039 ; and references cited therein
    • 3b Moon S.-H, Jung Y, Kim SH, Kim I. Bioorg. Med. Chem. Lett. 2016; 26: 110
    • 3c Mordhorst T, Bickmeyer U. Tetrahedron Lett. 2015; 56: 4363
    • 3d Meghasham NN, Mahesh KG, Pravin KG. World J. Pharm. Res. 2014; 3: 1064
    • 3e Ouyang J, Huang W, Yu W, Xiong W, Mula RV. R, Zou H, Yu Y. Chem.-Biol. Interact. 2014; 208: 1
    • 3f Ong CW, Yang Y.-T, Liu M.-C, Fox KR, Liu PH, Tung H.-W. Org. Biomol. Chem. 2012; 10: 1040
    • 3g Drozdowska D. Molecules 2011; 16: 3066
    • 3h Juguet M, Lautru S, Francou F.-X, Nezbedová Š, Leblond P, Gondry M, Pernodet J.-L. Chem. Biol. 2009; 16: 421
    • 3i Mohamed MS, El-Domany RA, El-Hameed RH. Acta Pharm. 2009; 59: 145
    • 3j Wakabayashi K.-i, Imai K, Miyachi H, Hashimoto Y, Tanatani A. Bioorg. Med. Chem. 2008; 16: 6799
    • 3k Arthur CR, Gupton JT, Kellogg GE, Yeudall WA, Cabot MC, Newsham IF, Gewirtz DA. Biochem. Pharmacol. 2007; 74: 981 ; and references cited therein
    • 3l David-Cordonnier M.-H, Hildebrand M.-P, Baldeyrou B, Lansiaux A, Keuser C, Benzschawel K, Lemster T, Pindur U. Eur. J. Med. Chem. 2007; 42: 752
    • 3m Bando T, Iida H, Tao Z.-F, Narita A, Fukuda N, Yamori T, Sugiyama H. Chem. Biol. 2003; 10: 751
    • 4a Kaur R, Rani V, Abbot V, Kapoor Y, Konar D, Kumar K. J. Pharm. Chem. Chem. Sci. 2017; 1: 17
    • 4b Gholap SS. Eur. J. Med. Chem. 2016; 110: 13
    • 4c Bhardwaj V, Gumber D, Abbot V, Dhiman S, Sharma P. RSC Adv. 2015; 5: 15233
    • 4d Domagala A, Jarosz T, Lapkowski M. Eur. J. Med. Chem. 2015; 100: 176
    • 4e Joshi SD, More UA, Kulkarni VH, Aminabhavi TM. Curr. Org. Chem. 2013; 17: 2279
    • 4f Ionescu RE, Gondran C, Cosnier S, Gheber LA, Marks RS. Talanta 2005; 66: 15
    • 5a Alfonso M, Tárraga A, Molina P. Tetrahedron Lett. 2016; 57: 3053
    • 5b Loudet A, Burgess K. Chem. Rev. 2007; 107: 4891
    • 5c Estrany F, Aradilla D, Oliver R, Alemán C. Eur. Polym. J. 2007; 43: 1876
    • 5d Najar SS, Kaynak A, Foitzik RC. Synth. Met. 2007; 157: 1
    • 5e Ko S, Jang J. Biomacromolecules 2007; 8: 182
    • 5f Tu X, Xie Q, Jiang S, Yao S. Biosens. Bioelectron. 2007; 22: 2819
    • 5g Michalska A, Maksymiuk K. Talanta 2004; 63: 109
    • 5h Qu L, Shi G. Chem. Commun. 2003; 206
    • 5i Sessler JL, Camiolo S, Gale PA. Coord. Chem. Rev. 2003; 240: 17
    • 5j Eichen Y, Nakhmanovich G, Epshtein O, Ehrenfreund E. J. Phys. Chem. B 2000; 104: 770
    • 6a Wang X.-F, Kitao O, Zhou H, Tamiaki H, Sasaki S.-i. Chem. Commun. 2009; 1523
    • 6b Chandra T, Brown KL. Tetrahedron 2008; 64: 9
    • 6c Squier AH, Hodgson DA, Keely BJ. Chem. Commun. 2003; 624
    • 6d Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC. Nat. Prod. Rep. 2002; 19: 390
    • 6e Rüdiger W. Phytochemistry 1997; 46: 1151
    • 6f Battersby AR. Nat. Prod. Rep. 1987; 4: 77
    • 7a Zidar N, Montalvão S, Hodnik Ž, Nawrot DA, Žula A, Ilaš J, Kikelj D, Tammela P, Mašič LP. Mar. Drugs 2014; 12: 940 ; and references cited therein
    • 7b Al-Mourabit A, Zancanella MA, Tilvi S, Romo D. Nat. Prod. Rep. 2011; 28: 1229
    • 7c Shinohara K, Bando T, Sugiyama H. Anticancer Drugs 2010; 21: 228
    • 7d Forte B, Malgesini B, Piutti C, Quartieri F, Scolaro A, Papeo G. Mar. Drugs 2009; 7: 705
    • 7e Fan H, Peng J, Hamann MT, Hu J.-F. Chem. Rev. 2008; 108: 264
    • 7f O’Malley DP, Li K, Maue M, Zografos AL, Baran PS. J. Am. Chem. Soc. 2007; 129: 4762
    • 7g Bally C. Curr. Med. Chem.: Anti-Cancer Agents 2004; 4: 363
    • 7h Fürstner A. Angew. Chem. Int. Ed. 2003; 42: 3582
    • 7i LeQuesne PW, Dong Y, Blythe TA. Recent Research on Pyrrole Alkaloids. In Alkaloids: Chemical and Biological Perspectives, Vol. 13. Pelletier SW. Elsevier; Amsterdam: 1999: 237
    • 8a Mohamed MS, Ali SA, Abdelaziz DH. A, Fathallah SS. BioMed Res. Int. 2014; 249780 ; and references cited therein
    • 8b Mohamed MS, Fathallah SS. Mini-Rev. Org. Chem. 2014; 11: 477
    • 8c Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
    • 9a Demeter LM, Shafer RW, Meehan PM, Holden-Wiltse J, Fischl MA, Freimuth WW, Para MF, Reichman RC. Antimicrob. Agents Chemother. 2000; 44: 794
    • 9b Cheng CL, Smith DE, Carver PL, Cox SR, Watkins PB, Blake DS, Kauffman CA, Meyer KM, Amidon GL, Stetson PL. Clin. Pharmacol. Ther. 1997; 61: 531
    • 9c Davey RT. Jr, Chaitt DG, Reed GF, Freimuth WW, Herpin BR, Metcalf JA, Eastman PS, Falloon J, Kovacs JA, Polis MA, Walker RE, Masur H, Boyle J, Coleman S, Cox SR, Wathen L, Daenzer CL, Lane HC. Antimicrob. Agents Chemother. 1996; 40: 1657
    • 9d Freimuth WW. Adv. Exp. Med. Biol. 1996; 394: 279
    • 10a Baraldi PG, Romagnoli R, Pavani MG, del Carmen Nunez M, Bingham JP, Hartley JA. Bioorg. Med. Chem. 2002; 10: 1611
    • 10b Beran M, Jeha S, O’Brien S, Estey E, Vitek L, Zurlo MG, Rios MB, Keating M, Kantarjian H. Clin. Cancer Res. 1997; 3: 2377
    • 11a Szerszenowicz J, Drozdowska D. Molecules 2014; 19: 11300
    • 11b Fang Y.-Y, Morris VR, Lingani GM, Long EC, Southerland WM. Open Conf. Proc. J. 2010; 1: 157
    • 11c Marcotte F.-A, Lubell WD. Org. Lett. 2002; 4: 2601
    • 11d Flanagan ME, Rollins SB, Williams RM. Chem. Biol. 1995; 2: 147
    • 11e Zimmer C, Wähnert U. Prog. Biophys. Mol. Biol. 1986; 47: 31
    • 11f Rajagopalan M, Ayyer J, Sasisekharan V. J. Biosci. 1985; 7: 27
    • 11g Kopka ML, Yoon C, Goodsell D, Pjura P, Dickerson RE. J. Mol. Biol. 1985; 183: 553
    • 12a Lohray BB, Lohray V. Pure Appl. Chem. 2005; 77: 179
    • 12b McCrindle BW, Ose L, Marais AD. J. Pediatr. 2003; 143: 74
    • 13a Biava M, Porretta GC, Manetti F. Mini-Rev. Med. Chem. 2007; 7: 65
    • 13b Biava M, Porretta GC, Deidda D, Pompei R, Tafi A, Manetti F. Bioorg. Med. Chem. 2003; 11: 515
    • 13c Deidda D, Lampis G, Fioravanti R, Biava M, Porretta GC, Zanetti S, Pompei R. Antimicrob. Agents Chemother. 1998; 42: 3035
    • 14a Raimondi MV, Listro R, Cusimano MG, La Franca M, Faddetta T, Gallo G, Schillaci D, Collina S, Leonchiks A, Barone G. Bioorg. Med. Chem. 2019; 27: 721
    • 14b McGuire TR, Coulter DW, Bai D, Sughroue JA, Li J, Yang Z, Qiao Z, Liu Y, Murry DJ, Chhonker YS, McIntyre EM, Alexander G, Sharp JG, Li R. BMC Cancer 2019; 19: 837
    • 14c Ding X.-B, Brimble MA, Furkert DP. Org. Biomol. Chem. 2016; 14: 5390
    • 14d Liu Y.-X, Zhang P.-X, Li Y.-Q, Song H.-B, Wang Q.-M. Mol. Diversity 2014; 18: 593
    • 14e Zhang X, Parry RJ. Antimicrob. Agents Chemother. 2007; 51: 946
    • 15a Brodhagen M, Henkels MD, Loper JE. Appl. Environ. Microbiol. 2004; 1758
    • 15b Thomas MG, Burkart MD, Walsh CT. Chem. Biol. 2002; 9: 171
    • 16a Kilani J, Fillinger S. Front. Microbiol. 2016; 7: 2014
    • 16b Park JY, Oh SA, Anderson AJ, Neiswender J, Kim J.-C, Kim YC. Lett. Appl. Microbiol. 2011; 52: 532
    • 16c van Pée K.-H, Ligon JM. Nat. Prod. Rep. 2000; 17: 157
    • 17a Tarasova OA, Nedolya NA, Albanov AI, Trofimov BA. Eur. J. Org. Chem. 2018; 5961
    • 17b Estevéz V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2014; 43: 4633
    • 17c Liu P, Liu J.-l, Wang H.-s, Pan Y.-m, Liang H, Chen Z.-F. Chem. Commun. 2014; 50: 4795
    • 17d Kucukdisli M, Ferenc D, Heinz M, Wiebe C, Opatz T. Beilstein J. Org. Chem. 2014; 10: 466
    • 17e Nedolya NA, Brandsma L, Trofimov BA. Synthesis 2013; 45: 93
    • 17f Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2010; 39: 4402
    • 17g Muzalevskiy VM, Shastin AV, Balenkova ES, Haufe G, Nenajdenko VG. Synthesis 2009; 3905
    • 17h Mathew P, Asokan CV. Tetrahedron 2006; 62: 1708
    • 17i Reisser M, Maas G. J. Org. Chem. 2004; 69: 4913
    • 18a Patel M, Saunthwal RK, Verma AK. Acc. Chem. Res. 2017; 50: 240
    • 18b Trofimov BA, Mikhaleva AI, Schmidt EYu, Sobenina LN. Chemistry of Pyrroles; CRC Press-Taylor & Francis Group: Boca-Raton, 2014
    • 18c Molchanov AP, Savinkov RS, Stepakov AV, Starova GL, Kostikov RR, Barnakova VS, Ivanov AV. Synthesis 2014; 46: 771
    • 18d Lan T, Chen X, Liu Z, Mao Z. J. Heterocycl. Chem. 2013; 50: 1094
    • 18e Verma AK, Joshi M, Prakash Singh V. Org. Lett. 2011; 13: 1630
    • 18f Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA. Tetrahedron Lett. 2010; 51: 5316
    • 18g Wang W, Yu D, Tian F. J. Lumin. 2010; 130: 494
    • 18h Liao Q, Wang Y, Zhang L, Xi C. J. Org. Chem. 2009; 74: 6371
    • 18i Wang W, Yu D, Tian F. Synth. Met. 2008; 158: 717
    • 18j Pinho e Melo TM. V. D, Soares MI. L, d’A Rocha Gonsalves AM, Paixão JA, Beja AM, Silva MR. J. Org. Chem. 2005; 70: 6629
    • 18k Movassaghi M, Ondrus AE. J. Org. Chem. 2005; 70: 8638
    • 18l Lea Z.-G, Chen Z.-C, Hu Y, Zheng Q.-G. Synthesis 2004; 1951
    • 18m Lebedev AY, Izmer VV, Kazyul’kin DN, Beletskaya IP, Voskoboynikov AZ. Org. Lett. 2002; 4: 623
    • 18n Varlamov AV, Borisova TN, Voskressensky LG, Nsabimana B, Chernyshev AI. Heterocycl. Commun. 2001; 7: 461
    • 18o Dubois CJ, Mccarley RL. J. Electroanal. Chem. 1998; 454: 99
    • 18p Settambolo R, Mariani M, Caiazzo A. J. Org. Chem. 1998; 63: 10022
    • 18q Hegyes P, Dispa J.-F, Hevesi L, Jeanmart L, de Mahieu A.-F, Jamber B, Devaux J. Polymer 1996; 37: 1493
    • 18r Hlavaty J, Papez V, Kavan L, Krtil P. Synth. Met. 1994; 66: 165
    • 18s Cagnolati R, Lucchesi M, Rolla PA, Castelvetro V, Ciardelli F, Colligiani A. Synth. Met. 1992; 46: 127
    • 18t Cooper G, Irwin WJ, Wheeler DL. Tetrahedron Lett. 1971; 12: 4321
    • 18u Shostakovskii MF, Skvortsova GG, Domnina ES. Russ. Chem. Rev. 1969; 38: 407
    • 19a Kishbaugh TL. S. Top. Heterocycl. Chem. 2012; 29: 1
    • 19b Chinchilla R, Nájera C, Yus M. Chem. Rev. 2004; 104: 2667
    • 19c Brandsma L, Verkruijsse H. Preparative Polar Organometallic Chemistry, Vol. 1. Springer; Berlin: 1987
    • 19d Fritzsche R, Seidel F, Rüffer T, Buschbeck R, Jakob A, Freitag H, Zahn DR. T, Lang H, Mehring M. J. Organomet. Chem. 2014; 755: 86
    • 19e Fogassy K, Kovács K, Keserű GM, Tőke L, Faigl F. J. Chem. Soc., Perkin Trans. 1 2001; 1039
    • 19f Brittain JM, Judith M, Jones RA, Arques JS, Saliente TA. Synth. Commun. 1982; 12: 231
    • 19g Hasan I, Marinelli ER, Lin L.-CC, Fowler FW, Levy AB. J. Org. Chem. 1981; 46: 157
  • 20 Mal’kina AG, Tarasova OA, Verkruijsse HD, van der Kerk AC. H. T. M, Brandsma L, Trofimov BA. Recl. Trav. Chim. Pays-Bas 1995; 114: 18
  • 21 Fleming P, O’Shea DF. J. Am. Chem. Soc. 2011; 133: 1698
    • 22a Tarasova OA, Taherirastgar F, Verkruijsse HD, Mal’kina AG, Brandsma L, Trofimov BA. Recl. Trav. Chim. Pays-Bas 1996; 115: 145
    • 22b Tarasova OA, Brandsma L, Verkruijsse HD, Mal’kina AG, Trofimov BA. Zh. Org. Khim. 1996; 32: 1208; in Russian
    • 22c Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA. Eur. J. Org. Chem. 2018; 1953
    • 22d Tarasova OA, Brandsma L, Nedolya NA. Abstracts of 1st All-Russian Conference of Chemistry of Heterocycles in Memory of A. N. Kost. Suzdal; Russia: 2000: 372, in Russian
    • 22e Tarasova OA, Nedolya NA, Albanov AI, Trofimov BA. Russ. J. Org. Chem. 2017; 53: 305
    • 22f Nedolya NA, Tarasova OA, Volostnykh OG, Albanov AI, Klyba LV, Trofimov BA. Synthesis 2011; 2192
    • 22g Brandsma L, Zwikker JW. Sci. Synth. 2005; 8a: 271
    • 23a Trofimov BA, Tarasova OA, Shemetova MA, Afonin AV, Klyba LV, Baikalova LV, Mikhaleva AI. Russ. J. Org. Chem. 2003; 39: 408
    • 23b Trofimov BA, Tarasova OA, Mikhaleva AI, Kalinina NA, Sinegovskaya LM, Henkelmann J. Synthesis 2000; 1585
  • 24 Brandsma L. Preparative Polar Organometallic Chemistry, Vol. 2. Springer; Berlin: 1990: 7