One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition–Elimination/Palladium-Catalyzed Buchwald–Hartwig Amination Reaction

Yinghua Wang; Hanyu Liang; Chunxia Chen; Deqiang Wang; Jinsong Peng

doi:10.1055/s-0034-1380496

Synthesis, Table of Contents

Synthesis 2015; 47(13): 1851-1860
DOI: 10.1055/s-0034-1380496

paper

One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition–Elimination/Palladium-Catalyzed Buchwald–Hartwig Amination Reaction

Yinghua Wang

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China Email: jspeng1998@nefu.edu.cn Email: 080122@nefu.edu.cn

,

Hanyu Liang

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China Email: jspeng1998@nefu.edu.cn Email: 080122@nefu.edu.cn

,

Chunxia Chen*

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China Email: jspeng1998@nefu.edu.cn Email: 080122@nefu.edu.cn

,

Deqiang Wang

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China Email: jspeng1998@nefu.edu.cn Email: 080122@nefu.edu.cn

,

Jinsong Peng*

Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, P. R. of China Email: jspeng1998@nefu.edu.cn Email: 080122@nefu.edu.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

A convenient approach has been developed for the construction of quinolin-4(1H)-one frameworks, starting from (Z)-β-chlorovinyl aromatic ketones and amines. Intermolecular Michael addition of an amine to a (Z)-β-chlorovinyl ketone was followed by elimination of a chloride anion to give enamine intermediates, with full retention of the initial Z-configuration. The enamine intermediates were transformed into quinolin-4(1H)-one products by a palladium-catalyzed intramolecular N-arylation in a tandem one-pot manner, with good to excellent yields.

Key words

quinolines - ketones - Michael additions - aminations - tandem reactions - cyclizations

Full Text

References

References

1a Höfle G, Kunze B. J. Nat. Prod. 2008; 71: 1843
1b Abe H, Kawada M, Inoue H, Ohba S.-i, Nomoto A, Watanabe T, Shibasaki M. Org. Lett. 2013; 15: 2124
1c Jadulco RC, Pond CD, Van Wagoner RM, Koch M, Gideon OG, Matainaho TK, Piskaut P, Barrows LR. J. Nat. Prod. 2014; 77: 183

2a Krishnamurthy M, Gooch BD, Beal PA. Org. Lett. 2004; 6: 63
2b Krishnamurthy M, Simon K, Orendt AM, Beal PA. Angew. Chem. Int. Ed. 2007; 46: 7044
2c Cross RM, Manetsch R. J. Org. Chem. 2010; 75: 8654
2d Audisio D, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. J. Org. Chem. 2011; 76: 4995
2e Chen F, Feng Z, He C.-Y, Wang H.-Y, Guo Y.-l, Zhang X. Org. Lett. 2012; 14: 1176
2f Klier L, Bresser T, Nigst TA, Karaghiosoff K, Knochel P. J. Am. Chem. Soc. 2012; 134: 13584

3a Chen Y.-L, Fang K.-C, Sheu J.-Y, Hsu S.-L, Tzeng C.-C. J. Med. Chem. 2001; 44: 2374
3b Asahina Y, Iwase K, Iinuma F, Hosaka M, Ishizaki T. J. Med. Chem. 2005; 48: 3194
3c Odagiri T, Inagaki H, Sugimoto Y, Nagamochi M, Miyauchi RN, Kuroyanagi J, Kitamura T, Komoriya S, Takahashi H. J. Med. Chem. 2013; 56: 1974

4a Li L, Wang H.-K, Kuo S.-C, Wu T.-S, Mauger A, Lin CM, Hamel E, Lee K.-H. J. Med. Chem. 1994; 37: 3400
4b Nakamura S, Kozuka M, Bastow KF, Tokuda H, Nishino H, Suzuki M, Tatsuzaki J, Natschke SL. M, Kuo S.-C, Lee K.-H. Bioorg. Med. Chem. 2005; 13: 4396
4c Chang Y.-H, Hsu M.-H, Wang S.-H, Huang L.-J, Qian K, Morris-Natschke SL, Hamel E, Kuo S.-C, Lee K.-H. J. Med. Chem. 2009; 52: 4883

5a Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. J. Med. Chem. 2010; 53: 7076
5b Cross RM, Namelikonda NK, Mutka TS, Luong L, Kyle DE, Manetsch R. J. Med. Chem. 2011; 54: 8321
5c Zhang Y, Clark JA, Connelly MC, Zhu F, Min J, Guiguemde WA, Pradhan A, Iyer L, Furimsky A, Gow J, Parman T, Mazouni FE, Phillips MA, Kyle DE, Mirsalis J, Guy RK. J. Med. Chem. 2012; 55: 4205

6a Sui Z, Nguyen VN, Altom J, Fernandez J, Hilliard JJ, Bernstein JI, Barrett JF, Ohemeng KA. Eur. J. Med. Chem. 1999; 34: 381
6b Xia Y, Yang Z.-Y, Xia P, Hackl T, Hamel E, Mauger A, Wu J.-H, Lee K.-H. J. Med. Chem. 2001; 44: 3932
6c Hadjeri M, Peiller EL, Beney C, Deka N, Lawson MA, Dumontet C, Boumendjel A. J. Med. Chem. 2004; 47: 4964

7a Cecchetti V, Parolin C, Moro S, Pecere T, Filipponi E, Calistri A, Tabarrini O, Gatto B, Palumbo M, Fravolini A, Palu G. J. Med. Chem. 2000; 43: 3799
7b Sato M, Motomura T, Aramaki H, Matsuda T, Yamashita M, Ito Y, Kawakami H, Matsuzaki Y, Watanabe W, Yamataka K, Ikeda S, Kodama E, Matsuoka M, Shinkai H. J. Med. Chem. 2006; 49: 1506
7c Pasquini S, Mugnaini C, Tintori C, Botta M, Trejos A, Arvela RK, Larhed M, Witvrouw M, Michiels M, Christ F, Debyser Z, Corelli F. J. Med. Chem. 2008; 51: 5125

8a Reitsema RH. Chem. Rev. 1948; 43: 43
8b López SE, Rebollo O, Salazar J, Charris JE, Yánez C. J. Fluorine Chem. 2003; 120: 71
8c Boteva AA, Krasnykh OP. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 757
8d Romek A, Opatz T. Eur. J. Org. Chem. 2010; 5841
8e Liu Q.-L, Li Q.-L, Fei X.-D, Zhu Y.-M. ACS Comb. Sci. 2011; 13: 19
8f Zhao J, Zhao Y, Fu H. Org. Lett. 2012; 14: 2710
8g Iaroshenko VO, Knepper I, Zahid M, Dudkin S, Kuzora R, Villinger A, Langer P. Org. Biomol. Chem. 2012; 10: 2955
8h Shao J, Huang X, Hong X, Liu B, Xu B. Synthesis 2012; 44: 1798
8i Victor NJ, Muraleedharan KM. Adv. Synth. Catal. 2014; 356: 3600

9 Camps R. Ber. Dtsch. Chem. Ges. 1899; 32: 3228

10a Li JJ. Name Reactions: A Collection of Detailed Reaction Mechanisms. 2nd ed. Springer; Berlin: 2003: 81
10b Zewge D, Chen C.-y, Deer C, Dormer PG, Hughes DL. J. Org. Chem. 2007; 72: 4276

11a Niementowski S. Ber. Dtsch. Chem. Ges. 1894; 27: 1394
11b Fuson RC, Burness DM. J. Am. Chem. Soc. 1946; 68: 1270
11c Son JK, Kim SI, Jahng Y. Heterocycles 2001; 55: 1981

12a Kalinin VN, Shostakovsky MV, Ponomaryov AB. Tetrahedron Lett. 1992; 33: 373
12b Torii S, Okumoto H, Xu LH, Sadakane M, Shostakovsky MV, Ponomaryov AB, Kalinin VN. Tetrahedron 1993; 49: 6773
12c Haddad N, Tan J, Farina V. J. Org. Chem. 2006; 71: 5031
12d Huang J, Chen Y, King AO, Dilmeghani M, Larsen RD, Faul MM. Org. Lett. 2008; 10: 2609
12e Zhao T, Xu B. Org. Lett. 2010; 12: 212
12f Takahashi I, Morita F, Kusagaya S, Fukaya H, Kitagawa O. Tetrahedron: Asymmetry 2012; 23: 1657
12g Iaroshenko VO, Knepper I, Zahid M, Kuzora R, Dudkin S, Villinger A, Langer P. Org. Biomol. Chem. 2012; 10: 2955
12h Fei X.-D, Zhou Z, Li W, Zhu Y.-M, Shen J.-K. Eur. J. Org. Chem. 2012; 3001
12i Iaroshenko VO, Zahid M, Mkrtchyan S, Gevorgyan A, Altenburger K, Knepper I, Villinger A, Sosnovskikh VY, Langer P. Tetrahedron 2013; 69: 2309

13a Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
13b Bernini R, Cacchi S, Fabrizi G, Sferrazza A. Synthesis 2009; 1209

14 Seppänen O, Muuronen M, Helaja J. Eur. J. Org. Chem. 2014; 4044

15a Peng J, Shang G, Chen C, Miao Z, Li B. J. Org. Chem. 2013; 78: 1242
15b Chen C, Shang G, Zhou J, Yu Y, Li B, Peng J. Org. Lett. 2014; 16: 1872
15c Peng J, Zhao Y, Zhou J, Ding Y, Chen C. Synthesis 2014; 46: 2051

16a Wang B, Wang S, Li P, Wang L. Chem. Commun. 2010; 46: 5891
16b Gandeepan P, Parthasarathy K, Su T.-H, Cheng C.-H. Adv. Synth. Catal. 2012; 354: 457

17a Pohland AE, Benson WR. Chem. Rev. 1966; 66: 161
17b Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2009; 48: 9592 ; Angew. Chem. 2009, 121, 9770

For selected examples in which β-halovinyl ketones or analogues are used as electrophilic coupling reagents, see:

18a Xiang JS, Mahadevan A, Fuchs PL. J. Am. Chem. Soc. 1996; 118: 4284
18b Paley RS, de Dios A, Estroff LA, Lafontaine JA, Montero C, McCulley DJ, Rubio MB, Ventura MP, Weers HL, Fernández de la Pradilla R, Castro S, Dorado R, Morente M. J. Org. Chem. 1997; 62: 6326
18c Xi C, Kotora M, Nakajima K, Takahashi T. J. Org. Chem. 2000; 65: 945
18d Kotora M, Matsumura H, Gao G, Takahashi T. Org. Lett. 2001; 3: 3467
18e Haack T, Kurtkaya S, Snyder JP, Georg GI. Org. Lett. 2003; 5: 5019
18f Bekele T, Brunette SR, Lipton MA. J. Org. Chem. 2003; 68: 8471
18g Bates CG, Saejueng P, Doherty MQ, Venkataraman D. Org. Lett. 2004; 6: 5005
18h Liang G, Miller AK, Trauner D. Org. Lett. 2005; 7: 819
18i Iwai T, Fujihara T, Terao J, Tsuji Y. J. Am. Chem. Soc. 2012; 134: 1268

For selected examples of syntheses of nitrogen heterocycles through Pd-catalyzed double aminations, see:

19a Willis MC, Brace GN, Holmes IP. Angew. Chem. Int. Ed. 2005; 44: 403
19b Willis MC, Brace GN, Findlay TJ. K, Holmes IP. Adv. Synth. Catal. 2006; 348: 851
19c Fletcher AJ, Bax MN, Willis MC. Chem. Commun. 2007; 4764
19d Kuwahara A, Nakano K, Nozaki K. J. Org. Chem. 2005; 70: 413
19e Zhang X, Yang Y, Liang Y. Tetrahedron Lett. 2012; 53: 6406
19f Ueno A, Kitawaki T, Chida N. Org. Lett. 2008; 10: 1999
19g Zhou Y, Verkade JG. Adv. Synth. Catal. 2010; 352: 616

20a Chen Q.-H, Geng Z. Chin. Sci. Bull. 1993; 38: 791
20b Esteban J, Costa AM, Gómez À, Vilarrasa J. Org. Lett. 2008; 10: 65
20c Kashiwabara T, Fuse K, Hua R, Tanaka M. Org. Lett. 2008; 10: 5469
20d Souibgui A, Gaucher A, Marrot J, Bourdreux F, Aloui F, Ben Hassine B, Prim D. Tetrahedron 2014; 70: 3042
20e Clayden J, Greeves N, Warren S, Wothers P. Organic Chemistry . Oxford University Press; Oxford: 2001. Chap. 23, 585

21a Eaton PE, Stubbs CE. J. Am. Chem. Soc. 1967; 89: 5722
21b Kim HY, Li J.-Y, Oh K. J. Org. Chem. 2012; 77: 11132

22a Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
22b Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27

23 Shim SC, Chae SA, Lee DY, Lim HS, Kalinin VN. J. Korean Chem. Soc. 1994; 38: 774

Supplementary Material

Supporting Information