Metal- and Solvent-free Synthesis of Functionalized Dihydrooxa­zolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Ludmila A. Oparina; Nikita A. Kolyvanov; Igor A. Ushakov; Anastasiya G. Mal’kina; Alexander V. Vashchenko; Boris A. Trofimov

doi:10.1055/s-0037-1610319

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(06): 1445-1454
DOI: 10.1055/s-0037-1610319

paper

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxazolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Authors

Ludmila A. Oparina
Nikita A. Kolyvanov
Igor A. Ushakov
Anastasiya G. Mal’kina
Alexander V. Vashchenko
Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation eMail: boris_trofimov@irioch.irk.ru

Abstract

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Abstract

The reaction of 3H-indoles with tertiary propargylic alcohols to give functionalized dihydrooxazolo[3,2-a]indoles in good to excellent yields has been developed. This metal- and solvent-free, one-pot tandem assembly proceeds under mild conditions (22–60 °C) and is regio- and stereoselective: either the Z- or E-isomers (relative to the double bond) are alternatively formed depending on other functionalized substituents on the propargylic alcohols.

Key words

3H-indole - 1H-benzo[e]indole - propargylic alcohols - annulation - dihydrooxazolo[3,2-a]indoles

Volltext

Referenzen

References

1a Bunders C, Cavanagh J, Melander C. Org. Biomol. Chem. 2011; 9: 5476
1b Kaushik N, Kaushik N, Attri P, Kumar N, Kim C, Verma A, Choi E. Molecules 2013; 18: 6620
1c Yin L, Hu Q, Emmerich J, Lo MM.-C, Metzger E, Ali A, Hartmann RW. J. Med. Chem. 2014; 57: 5179
1d Al Osaimi AG, Ali RS, Saad HA, El Sayed Aly MR. Russ. J. Gen. Chem. 2017; 87: 1246
1e Ali RS, Saad HA. Molecules 2018; 23: 693

2a Kobayashi S, Peng G, Fukuyama T. Tetrahedron Lett. 1999; 40: 1519
2b Herold F, Krol M, Kleps J. Acta Pol. Pharm. 2004; 61: 139
2c Shimogawa H, Kuribayashi S, Teruya T, Suenaga K, Kigoshi H. Tetrahedron Lett. 2006; 47: 1409
2d Mohamed MS, El-Domany RA, El-Hameed RH. Acta Pharm. 2009; 59: 145 ; https://hrcak.srce.hr/acta-pharmaceutica
2e Jones SB, Simmons B, Mastracchio A, MacMillan DW. C. Nature (London) 2011; 475: 83
2f Suzuki T, Kubota T, Kobayashi J. Bioorg. Med. Chem. Lett. 2011; 21: 4220
2g Tiong S, Looi C, Hazni H, Arya A, Paydar M, Wong W, Cheah S.-C, Mustafa M, Awang K. Molecules 2013; 18: 9770
2h Ghorab MM, Alsaid MS. Biomed. Res. 2015; 26: 420
2i Allison BD, Branstetter BJ, Breitenbucher JG, Hack MD, Hawryluk NA, Lebsack AD, McClure KJ, Merit JE. US 20160318942, 2016

3a Sanguinet L, Pozzo J.-L, Rodriguez V, Adamietz F, Castet F, Ducasse L, Champagne B. J. Phys. Chem. B 2005; 109: 11139
3b Mancois F, Pozzo J.-L, Adamietz F, Rodriguez V, Ducasse L, Castet F, Plaquet A, Champagne B. Chem.–Eur. J. 2009; 15: 2560
3c Szalóki G, Alévêque O, Pozzo J.-L, Hadji R, Levillain E, Sanguinet L. J. Phys. Chem. B 2015; 119: 307
3d Bondu F, Quertinmont J, Rodriguez V, Pozzo J.-L, Plaquet A, Champagne B, Castet F. Chemistry 2015; 21: 18749
3e Pielak K, Bondu F, Sanguinet L, Rodriguez V, Champagne B, Castet F. J. Phys. Chem. C 2017; 121: 1851

4a Mancois F, Sanguinet L, Pozzo J.-L, Guillaume M, Champagne B, Rodriguez V, Adamietz F, Ducasse L, Castet F. J. Phys. Chem. B 2007; 111: 9795
4b Sevez G, Gan J, Delbaere S, Vermeersch G, Sanguinet L, Levilain E, Pozzo J.-L. Photochem. Photobiol. Sci. 2010; 9: 131
4c Szaloki G, Sanguinet L. In Photon-Working Switches . Yokoyama Y, Nakatani K. Springer; Tokyo: 2017: 69

5a Buinauskaitė V, Martynaitis V, Mangelinckx S, Kreiza G, De Kimpe N, Šačkus A. Tetrahedron 2012; 68: 9260
5b Steponavičiūtė R, Martynaitis V, Bieliauskas A, Šačkus A. Tetrahedron 2014; 70: 1967
5c Ščerbtkaitè E, Tamulienè R, Bieliauskas A, Šačkus A. Molbank 2017; M944

6a Nguyen TM, Duong HA, Richard JA, Johannes CW, Pincheng F, Ye DK. J, Shuying EL. Chem. Commun. 2013; 49: 10602
6b Fong JZ. M, Choo SS. S, Richard JA, Garland MV, Guo L, Johannes CW, Nguyen TM. Eur. J. Org. Chem. 2015; 995

7a Gu Y, Fei X, Liu Y, Wang Y, Yang X. J. Lumin. 2013; 134: 184
7b Guo L, Chan MS, Xu D, Tam DY, Bolze F, Lo PK, Wong MS. ACS Chem. Biol. 2015; 10: 1171
7c Bricks J, Kachkovskii A, Slominskii Y, Gerasov A, Popov S. Dyes Pigm. 2015; 121: 238
7d Soriano E, Holder C, Levitz A, Henary M. Molecules 2015; 21: 23
7e Levitz A, Marmarchi F, Henary M. Molecules 2018; 23: 226

8a Bouteiller C, Clavé G, Bernardin A, Chipon B, Massonneau M, Renard P.-Y, Romieu A. Bioconjugate Chem. 2007; 18: 1303
8b Kvach MV, Ustinov AV, Stepanova IA, Malakhov AD, Skorobogatyi MV, Shmanai VV, Korshun VA. Eur. J. Org. Chem. 2008; 2107
8c Owens EA, Henary M, El Fakhri G, Choi HS. Acc. Chem. Res. 2016; 49: 1731

9a Schaafsma BE, Mieog JS. D, Hutteman M, Van der Vorst JR, Kuppen PJ, Löwik CW, Frangioni JV, van de Velde CJ, Vahrmeijer AL. J. Surg. Oncol. 2011; 104: 323
9b Aoyama K, Kamio T, Ohchi T, Nashizawa M, Kamioka S. World J. Surg. Oncol. 2011; 9: 157
9c Liu J, Huang L, Wang N, Chen P. J. Int. Med. Res. 2017; 45: 514
9d Thomas AP, Palanikumar L, Jeena MT, Kim K, Ryu J.-H. Chem. Sci. 2017; 8: 8351
9e Bhattarai P, Dai Z. Adv. Healthcare Mater. 2017; 17002

10a Zhang D, Su J, Ma X, Tian H. Tetrahedron 2008; 64: 8515
10b Zhou X, Wu X, Yoon J. Chem. Commun. 2015; 51: 111
10c Erbas-Cakmak S, Kolemen S, Sedgwick AC, Gunnlaugsson T, James TD, Yoon J, Akkaya EU. Chem. Soc. Rev. 2018; 47: 2228

11a Raymo FM, Giordani S. J. Am. Chem. Soc. 2002; 124: 2004
11b Guo X, Zhang D, Zhang G, Zhu D. J. Phys. Chem. B 2004; 108: 11942
11c Kaur P, Kaur S, Singh K, Sharma PR, Kaur T. Dalton Trans. 2011; 40: 10818
11d Minkin VI. In Molecular Switches . 2nd ed., Vol. 1; Feringa BL, Browne WR. Wiley-VCH; Weinheim: 2011: 37
11e Yuan L, Lin W, Yang Y, Chen H. J. Am. Chem. Soc. 2012; 134: 1200

12a Burke A, Schmidt-Mende L, Ito S, Gratzel M. Chem. Commun. 2007; 234
12b Yousuke O, Yutaka H. Eur. J. Org. Chem. 2009; 2903
12c Kim JY, Kim YH, Kim YS. Curr. Appl. Phys. 2011; 11: S117
12d Mozhgan H, Kamaladin G. Pigm. Resin Technol. 2017; 46: 393
12e Meyenburg I, Hofeditz N, Ruess R, Rudolph M, Schlettwein D, Heimbrodt W. AIP Adv. 2018; 8: 055218

13a Bartnic R, Lesniak S, Mloston G, Zielinski T, Gebiski K. Chem. Stosow. 1990; 34: 325
13b Bartnic R, Mloston G, Gebulska Z. Chem. Stosow. 1990; 34: 343
13c Raue R. In Ulmann’s Encyclopedia of Industrial Chemistry . 5th ed., Vol. A16; Elvers B, Hawkins S, Schultz G. VCH; Weinheim: 1990: 487
13d Petkov I, Charra F, Nunzi JM, Deligeorgiev T. J. Photochem. Photobiol. A: Chem. 1999; 128: 93

14a Miller SI, Tanaka R. In Selective Organic Transformations . Vol. 1. Thyagarajan BS. Wiley Interscience; New York: 1970: 143
14b Dickstein JI, Miller SI. In The Chemistry of the Carbon-Carbon Triple Bond, Part 2 . Patai S. Wiley Interscience; Chichester: 1978: 843

15 Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123
16 Amslinger S, Lindner SK. Synthesis 2011; 2671
17 CCDC 1852754 and 1852755 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
18 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112

19a Landor SR, Demetriou B, Grzeskowiak R, Pavey D. J. Organomet. Chem. 1975; 93: 129
19b Trofimov BA, Skvortsov YuM, Mal’kina AG, Gritsa AI. Zh. Org. Khim. 1985; 21: 2020 ; Chem. Abstr. 1986, 105, 78491s
19c Trofimov BA, Mal’kina AG, Gritsa AI, Skvortsov YuM, Stankevich VK, Sokolyanskaya LV. Zh. Obshch. Khim. 1996; 66: 106 ; Chem. Abstr. 1997, 126, 18567v
19d Chowdhury C, Kundu NG. Tetrahedron 1999; 55: 7011
19e Trofimov BA, Andriyankova LV, Shaikhudinova SI, Kazantseva TI, Mal’kina AG, Zhivet’ev SA, Afonin AV. Synthesis 2002; 853

Zusatzmaterial

Supporting Information (PDF)

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxa­zolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Authors

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxazolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols