[3+2] Cycloaddition of Masked o-Benzoquinones with Azomethine Ylides

Santhosh Kumar Chittimalla; Rajesh Kuppusamy; Anjan Chakrabarti

doi:10.1055/s-0031-129043

Synlett, Table of Contents

Synlett 2012; 23(13): 1901-1906
DOI: 10.1055/s-0031-129043

letter

[3+2] Cycloaddition of Masked o-Benzoquinones with Azomethine Ylides

Santhosh Kumar Chittimalla*

AMRI Singapore Research Centre, 61 Science Park Road, #05-01, The Galen, Science Park III, Singapore 117525, Singapore, Fax: +6563985511 Email: santhosh.chittimalla@amriglobal.com

,

Rajesh Kuppusamy

AMRI Singapore Research Centre, 61 Science Park Road, #05-01, The Galen, Science Park III, Singapore 117525, Singapore, Fax: +6563985511 Email: santhosh.chittimalla@amriglobal.com

,

Anjan Chakrabarti

AMRI Singapore Research Centre, 61 Science Park Road, #05-01, The Galen, Science Park III, Singapore 117525, Singapore, Fax: +6563985511 Email: santhosh.chittimalla@amriglobal.com

› Author Affiliations

Abstract

All articles of this category

Abstract

A simple and efficient access to highly functionalized isoindolone derivatives via a [3+2] cycloaddition process between in situ generated azomethine ylides with various stable (isolable) masked o-benzoquinones is described. This approach allows a rapid and general synthesis of isoindolones with substituents to further manipulate and elaborate the structural complexity.

Key words

masked o-benzoquinones - [3+2] cycloadditions - azomethine ylides - isoindolones - isoindolines

Full Text

References

References and Notes

1a Magdziak D, Meek SJ, Pettus TR. R. Chem. Rev. 2004; 104: 1383
1b Liao C.-C, Peddinti RK. Acc. Chem. Res. 2002; 35: 856
1c Singh V. Acc. Chem. Res. 1999; 32: 324

2a Hsu D.-S, Chou Y.-Y, Tung Y.-S, Liao C.-C. Chem. Eur. J. 2010; 16: 3121
2b Lu P.-H, Yang C.-S, Devendar B, Liao C.-C. Org. Lett. 2010; 12: 2642
2c Kao T.-C, Chuang GJ, Liao C.-C. Angew. Chem. Int. Ed. 2008; 47: 7325
2d Liao C.-C. Pure Appl. Chem. 2005; 77: 1221

3a Sacher JR, Weinreb SM. Tetrahedron 2011; 67: 10203
3b Mehta G, Maity P. Tetrahedron Lett. 2011; 52: 1749
3c Kobayashi S, Suzuki T. Org. Lett. 2010; 12: 2920
3d Cook SP, Polara A, Danishefsky SJ. J. Am. Chem. Soc. 2006; 128: 16440

4a Chittimalla SK, Shiao H.-Y, Liao C.-C. Org. Biomol. Chem. 2006; 4: 2267
4b Liao C.-C, Chu C.-S, Lee T.-H, Rao PD, Ko S, Song L.-D, Hsiao H.-C. J. Org. Chem. 1999; 64: 4102

5a Lai C.-H, Shen Y.-L, Wang M.-N, Rao NS. K, Liao C.-C. J. Org. Chem. 2002; 67: 6493
5b Yen C.-F, Peddinti RK, Liao C.-C. Org. Lett. 2000; 2: 2909

6a Liao C.-C, Wei C.-P. Tetrahedron Lett. 1991; 32: 4553
6b Hsieh M.-F, Rao PD, Liao C.-C. Chem. Commun. 1999; 1441
6c Hou H.-F, Peddinti RK, Liao C.-C. Org. Lett. 2002; 4: 2477
6d Runcie KA, Taylor RJ. K. Org. Lett. 2001; 3: 3237
6e McKillop A, Perry DH, Edwards M, Antus S, Farkas L, Nogradi M, Taylor EC. J. Org. Chem. 1976; 41: 282
6f Banwell MG, Collis MP. J. Chem. Soc., Chem. Commun. 1991; 1343
6g Mitchell AS, Russell RA. Tetrahedron 1997; 53: 4387

7a Tsuge O, Kanemasa S, Ohe M, Takenaka S. Bull. Chem. Soc. Jpn. 1987; 60: 4079
7b Joucla M, Martier J. J. Chem. Soc., Chem. Commun. 1985; 1566

8a Smith ND, Huang D, Cosford ND. P. Org. Lett. 2002; 4: 3537
8b Airaksinen AJ, Ahlgren M, Vepsalainen J. J. Org. Chem. 2002; 67: 5019
8c van Leusen AM, Siderius H, Hoogenboom BE, van Leusen D. Tetrahedron Lett. 1972; 52: 5337

9a Pokholenko AA, Voitenka ZV, Kovtunenko VA. Russ. Chem. Rev. 2004; 73: 771
9b Marinicheva GE, Gubina TI. Chem. Heterocycl. Compd. 2004; 40: 1517
9c Kovacs B, Pinegar LA. US 20090318520 A1, 2009
9d Concha-Herrera V, Vivo-Truyols G, Torres-Lapasio JR, Garcia-Alvarez-Coque MC. Anal. Chim. Acta 2004; 518: 191
9e Williams BJ, Williams M, Frederickson M. US 20110098290 A1, 28.04.2011
9f Jin Q. WO 2010102968 A1, 16.09.2010
9g Liu J, Yang Y, Ji R. Helv. Chim. Acta 2004; 87: 1935
9h Ishizumi K, Kojima A, Antoku F. Chem. Pharm. Bull. 1991; 39: 2288

10a Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
10b Najera C, Sangano JM. Curr. Org. Chem. 2003; 7: 1105
10c Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
10d Huisgen R. J. Org. Chem. 1976; 41: 403
10e Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565

11 Chittimalla SK, Liao C.-C. Tetrahedron 2003; 59: 4039
12 For example, when column purified compound 5c was subjected to the standard reaction conditions [sarcosine (1.0 equiv), paraformaldehyde (2.0 equiv), MgSO₄(1.5 equiv) in THF at reflux temperature for 12 h] aromatized product 7c was isolated in 40% yield as expected along with 10% unreacted starting material (remaining was a complex mixture by ¹H NMR analysis with no indication for the formation of other possible cycloaddition products).
13 Lin K.-C, Chittimalla SK, Peddinti RK, Liao C.-C. J. Chin. Chem. Soc. Taipei 2004; 51: 1037
14 For example, when compound 5d was treated with 4 N HCl in dioxane for 1 h furnished compound 7d (after NH₄OH wash) in quantitative yield (Scheme 3).

15a Ohmura T, Kijima A, Suginome M. Org. Lett. 2011; 13: 1238
15b Ahmed M, Kricka LJ, Vernon JM. J. Chem. Soc., Perkin Trans. 1 1975; 71