Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles

Lyubov N. Sobenina; Denis N. Tomilin; Igor A. Ushakov; Albina I. Mikhaleva; J. Sh. Ma; G. Yang; Boris A. Trofimov

doi:10.1055/s-0032-1318149

Synthesis, Table of Contents

Synthesis 2013; 45(5): 678-682
DOI: 10.1055/s-0032-1318149

paper

Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles

Authors

Lyubov N. Sobenina

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Denis N. Tomilin

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Igor A. Ushakov

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Albina I. Mikhaleva

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
J. Sh. Ma

^bBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
G. Yang

^bBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru
Boris A. Trofimov*

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

Abstract

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Abstract

2-Ethynyl-4,5,6,7-tetrahydroindoles, readily available from 4,5,6,7-tetrahydroindoles and bromoacetylenes on K₂CO₃, when treated with sodium azide in DMSO, afford functionalized tetrahydroindole-triazoles ensembles. The reaction proceeds under mild conditions (room temperature) to give triazoles with acyl or ester moieties in quantitative yields.

Key words

click chemistry - cycloaddition - alkynes - sodium azide - triazoles

Full Text

References

References

1a Kharb R, Sharma PCh, Yar MSh. J. Enzyme Inhib. Med. Chem. 2011; 26: 1
1b Singhal N, Sharma PK, Dudhe R, Kumar N. J. Chem. Pharm. Res. 2011; 3: 126

2a Bektaş H, Karaali N, Sahin D, Demirbaş A, Karaoglu SA, Demirbaş N. Molecules 2010; 15: 2427
2b Sumangala V, Poojary B, Chidananda N, Fernandes J, Kumari NS. Arch. Pharmacal. Res. 2010; 33: 1911
2c Pereira D, Fernandes P. Bioorg. Med. Chem. Lett. 2011; 21: 510

3a Savini L, Massarelli P, Chiasserini L, Pellerano C, Bruni G. Farmaco 1994; 49: 633
3b Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A. Bioorg. Med. Chem. Lett. 2004; 14: 6057
3c Ram JS. Rasayan J. Chem. 2009; 2: 706
3d Rajasekaran A, Rajagopal KA. Acta Pharm. 2009; 59: 355

4a Singh BK, Yadav AK, Kumar B, Gaikwad A, Sinha SK, Chaturvedi V, Tripathi RP. Carbohydr. Res. 2008; 343: 1153
4b Wilkinson BL, Long H, Sim E, Fairbanks AJ. Bioorg. Med. Chem. Lett. 2008; 18: 6265
4c Boechat N, Ferreira VF, Ferreira SB, de Lourdes G, Ferreira M, de C da Silva F, Bastos MM, Dos S, Costa M, Lourenço MC, Pinto AC, Krettli AU, Aguiar AC, Teixeira BM, da Silva NV, Martins PR, Bezerra FA, Camilo AL, da Silva GP, Costa CC. J. Med. Chem. 2011; 54: 5988

5a Zhou L, Amer A, Korn M, Burda R, Balzarini J, De Clercq E, Kern ER, Torrence PF. Antiviral Chem. Chemother. 2005; 16: 375
5b Jordão AK, Afonso PP, Ferreira VF, de Souza MC, Almeida MC, Beltrame CO, Paiva DP, Wardell SM, Wardell JL, Tiekink ER, Damaso CR, Cunha AC. Eur. J. Med. Chem. 2009; 44: 3777
5c Pérez-Castro I, Caamaño O, Fernández F, García MD, López C, de Clercq E. ARKIVOC 2010; (iii): 152

6a Holla BS, Poojary KN, Rao BS, Shivananda MK. Eur. J. Med. Chem. 2002; 37: 511
6b Holla BS, Veerendra B, Shivananda MK, Poojary B. Eur. J. Med. Chem. 2003; 38: 759
6c Reddy DM, Srinivas J, Chashoo G, Saxena AK, Kumar HM. S. Eur. J. Med. Chem. 2011; 46: 1983
6d Singh P, Raj R, Kumar V, Mahajan MP, Bedi PM, Kaur T, Saxena AK. Eur. J. Med. Chem. 2012; 47: 594
6e Li X, Lin Y, Yuan Y, Liu K, Qian X. Tetrahedron 2011; 67: 2299
6f Kumar D, Narayanam MK, Chang K.-H, Shah K. Chem. Biol. Drug Des. 2011; 77: 182

7 Kaur H, Kumar S, Lata S, Saxena KK, Kumar A. Eur. J. Med. Chem.

8a Aher NG, Pore VS, Mishra NN, Kumar A, Shukla PK, Sharma A, Bhat MK. Bioorg. Med. Chem. Lett. 2009; 19: 759
8b Wei J.-J, Jin L, Wan K, Zhou Ch.-He. Bull. Korean Chem. Soc. 2011; 32: 229
8c Sangshetti JN, Lokwani DK, Sarkate AP, Shinde DB. Chem. Biol. Drug Des. 2011; 78: 800
8d Morzherin Y, Prokhorova PE, Musikhin DA, Glukhareva TV, Fan Z. Pure Appl. Chem. 2011; 83: 715
8e Shalini K, Kumar N, Drabu S, Sharma PK. Beilstein J. Org. Chem. 2011; 7: 668
8f Wang XL, Wan K, Zhou CH. Eur. J. Med. Chem. 2010; 45: 4631

9 Schreier E. Helv. Chim. Acta 1976; 59: 585
10 Dong H.-S, Wei K, Wang Q.-L, Quan B, Zhang Z.-Y. J. Chin. Chem. Soc. 2000; 47: 343

11a The Merck Index . 12th ed.; Budavari S. Merck Co. Inc; White House Station, NJ: 1996
11b Haber J. Cas. Lek. Cesk. 2001; 140: 596

12a Mothes-Wagner U, Reitze HK, Seitz KA. Exp. Appl. Acarol. 1990; 8: 27
12b Pechacek JT. US Patent 6015826 A, 1998 ; Chem. Abstr. 2000, 132, 89499.
12c Jacobson RM, Mulvihill MJ, Liu Ch, Liu X. US Patent 6258751, 2001 ; Chem. Abstr. 2001, 134, 42133.

13a Quraishi MA, Danish J. J. Am. Oil Chem. Soc. 2000; 77: 1107
13b Quraishi MA, Sardar R. Corrosion 2002; 58: 748

14a Khanmohammadi H, Erfantalab M. Spectrochim. Acta, Part A 2012; 86: 39
14b Smith NW, Alonso A, Brown CM, Dzyuba SV. Biochem. Biophys. Res. Commun. 2010; 391: 1455

15 Guenther D, Nestler HJ, Roesher G, Schinzel E. Ger. Pat. 615164, 1980 ; Chem. Abstr. 1980, 93, 73786.

16a Bijev AT, Prodanova P. Chem. Heterocycl. Compd. 2007; 43: 306
16b Padmavathi V, Nagendra MohanA. V, Thriveni P, Shazia A. Eur. J. Med. Chem. 2009; 44: 2313

17 Sessler JL, Cai J, Gong H.-Y, Yang X, Arambula JF, Hay BP. J. Am. Chem. Soc. 2010; 132: 14058

18a Kamijo S, Jin T, Huo Z, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 7786
18b Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L. J. Org. Chem. 2005; 70: 6526
18c Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F. Angew. Chem. Int. Ed. 2006; 45: 6893
18d Jiang Y, Kuang C, Yang Q. Synthesis 2010; 4256
18e Kolarovič A, Schnürch M, Mihovilovic MD. J. Org. Chem. 2011; 76: 2613

19a Journet M, Cai D, Kowal JJ, Larsen RD. Tetrahedron Lett. 2001; 42: 9117
19b Katritzky AR, Singh SK. J. Org. Chem. 2002; 67: 9077
19c Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
19d Katritzky AR, Zhang Y, Singh SK. Heterocycles 2003; 60: 1225
19e Li J, Wang D, Zhang Y, Li J, Chen B. Org. Lett. 2009; 11: 3024
19f Wu L.-Y, Xie Y.-X, Chen Z.-S, Niu Y.-N, Liang Y.-M. Synlett 2009; 1453
19g Zhang W, Kuang C, Yang Q. Synthesis 2010; 283

20a Trofimov BA, Stepanova ZV, Sobenina LN, Mikhaleva AI, Ushakov IA. Tetrahedron Lett. 2004; 45: 6513
20b Stepanova ZV, Sobenina LN, Mikhaleva AI, Ushakov IA, Elokhina VN, Voronov VK, Trofimov BA. Synthesis 2004; 2736
20c Sobenina LN, Demenev AP, Mikhaleva AI, Ushakov IA, Vasil'tsov AM, Ivanov AV, Trofimov BA. Tetrahedron Lett. 2006; 47: 7139
20d Trofimov BA, Sobenina LN, Stepanova ZV, Demenev AP, Mikhaleva AI, Ushakov IA, Vakul'skaya TI, Petrova OV. Russ. J. Org. Chem. 2006; 42: 1348
20e Trofimov BA, Sobenina LN, Stepanova ZV, Ushakov IA, Petrova OV, Tarasova OA, Volkova KA, Mikhaleva AI. Synthesis 2007; 447
20f Trofimov BA, Sobenina LN, Demenev AP, Stepanova ZV, Petrova OV, Ushakov IA, Mikhaleva AI. Tetrahedron Lett. 2007; 48: 4661

21a Trofimov BA, Sobenina LN, Stepanova ZV, Vakul'skaya TI, Kazheva ON, Aleksandrov GG, Dyachenko OA, Mikhaleva AI. Tetrahedron 2008; 64: 5541
21b Trofimov BA, Sobenina LN, Stepanova ZV, Petrova OV, Ushakov IA, Mikhaleva AI. Tetrahedron Lett. 2008; 49: 3946

22a Trofimov BA, Mikhaleva АI. N-Vinylpyrroles . Nauka; Novosibirsk: 1984
22b Trofimov BA In Advances in Heterocyclic Chemistry . Vol. 51. Academic Press; New York: 1990: 177
22c Trofimov BA, Mikhaleva АI, Schmidt EYu, Ryapolov OA, Platonov VB. Russian Patent RU 2297410, 2006 ; Chem. Abstr. 2008, 146, 462130.

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