A new facile approach to isoindole and pyrrole derivatives

Synlett

Volumn , Issue 6, 2010, Pages 924-930

  Yasmin, Nasima ^a   Ray, Jayanta K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Amines; Isoindoles; Nitrogen heterocycles; Pyrroles; Synthetic method

Indexed keywords

3 ( 2 FORMYL CYCLOALKENYL)ALPHA,BETA UNSATURATED ESTER; 3 ( 2 FORMYL CYCLOALKENYL)NITRILE; ALDEHYDE DERIVATIVE; AMINE; BETA BROMOVINYL ALDEHYDE; ESTER DERIVATIVE; ISOINDOLE DERIVATIVE; NITRILE; PALLADIUM; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; HECK REACTION; MICHAEL ADDITION; RING OPENING; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 77949893188     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219563     Document Type: Article

References (60)

1. Sundberg R. J, Comprehensive Heterocyclic Chemistry Vol. 4, Katritzky A R., Rees C W., Pergamon Oxford 1984 313
2. Joule J A., Mills K, Heterocyclic Chemistry Blackwell Publishing Oxford 2000 237. 324
3. Joule J A., Mills K, Heterocyclic Chemistry Blackwell Publishing Oxford 2000 324
4. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
5. Portevin B, Tordjman C, Pastoreau P, Bonnet J, DeNanteuil G, J. Med. Chem. 2000 43 4582
6. Peterlin-Mai L, Mlinek G, Solmajer T, Trampu-Bakija A, Stegnard M, Kikelja D, Bioorg. Med. Chem. Lett. 2003 13 789
7. Mi B.-X, Wang P.-F, Liu M.-W, Kwong H.-L, Wong N B., Lee C.-S, Lee S.-T, Chem. Mater. 2003 15 3148
8. Ding Y, Hay A S., J. Polym. Sci., Part A: Polym. Chem. 1999 37 3293
9. Gauvin S, Santerre F, Dodelet J P., Ding Y, Hlil A R., Hay A S., Anderson J, Armstrong N R., Gorjanc T C., DIorio M, Thin Solid Films 1999 353 218
10. Matuszewski B K., Givens [nl]R S., Srinivasachar K, Carlson R G., Higuchi T, Anal. Chem. 1987 59 1102
11. Maurer A, Roberts B G., J. Am. Chem. Soc. 1967 89 4091
12. Chen Y.-L, Lee M H., Wong W.-Y, Lee A W. M., Synlett 2006 2510
13. Chen Z, Mller P, Swager T M., Org. Lett. 2006 8 273
14. LeHoullier C S., Gribble G W., J. Org. Chem. 1983 48 2364
15. Jacobi P A., Buddhu S C., Fry D, Rajeswari S, [nl] J. Org. Chem. 1997 62 2894
16. Fuhrhop J H., Hosseinpour D, Liebigs Ann. Chem. 1985 689
17. May D A., Lash T D., J. Org. Chem. 1992 57 4820
18. Finikova O, Cheprakov A, Beletskaya I, Vinogradov S, Chem. Commun. 2001 261
19. Portevin B, Tordjman C, Pastoureau P, Bonnet J, Nanteuil G D., J. Med. Chem. 2000 43 4582
20. Peterlin-Mai L, Mlinek G, olmajer T, Trampu-Bakija A, Stegnar M, Kikelj D, Bioorg. Med. Chem. Lett. 2003 13 789
21. Bach N J., Kornfeld E C., Jones N D., Chaney M O., Dorman D E., Paschal J W., Clemens J A., Smalstig E B., J. Med. Chem. 1980 23 481
22. Markushina I A., Marinicheva G E., Lebedev A A., Merkulova T B., USSR Patent (written in Russian) 19960310 1996;
23. Chem. Abstr. 1996, 126, 18788
24. Bonnaud B, Bigg D H., Synthesis 1994 465
25. Yagi T, Aoyama T, Shioiri T, Synlett 1997 1063
26. Jacobi P A., Buddhu S C., Tetrahedron Lett. 1988 29 4823
27. Peterlin-Mai L, Jurca A, Marinko P, Jancar A, Kikelj D, Tetrahedron 2002 58 1557
28. Gabbutt C D., Hepworth J D., Heron B M., Pugh S, J. Chem. Soc., Perkin Trans. 1 2002 2799
29. Bennes R, Babiloni M S., Hayes W, Philp D, Tetrahedron Lett. 2001 42 2377
30. Ansari M A., Craig J C., Synth. Commun. 1991 21 1971
31. Hombrecher H K., Horter G, Synthesis 1990 389
32. Rosjamp E J., Dragovich P S., Hartung J E., Pedersen S F., J. Org. Chem. 1989 54 4736
33. Paine J B. III, Brough J R., Buller K K., Erikson E E., J. Org. Chem. 1987 52 3986
34. Vicente M G. H., Tom A C., Walter A, Cavaleiro [nl]J A. S., Tetrahedron Lett. 1997 38 3639
35. Ando K, Kankake M, Suzuki T, Takayama H, Synlett 1994 741
36. Finikova O, Cheprakov A, Beletskaya I, Carroll P J., Vinogradov S, J. Org. Chem. 2004 69 522
37. Cheng W.-C, Olmstead M M., Kurth M J., J. Org. Chem. 2001 66 5528
38. Abel Y, Haake E, Haake G, Schmidt W, Struve D, Walter A, Montforts F.-P, Helv. Chim. Acta 1998 81 1978
39. Arnold D P., BurgessDean L, Hubbard J, Rahman M A., Aust. J. Chem. 1994 47 969
40. Haake G, Struve D, Montforts F P., Tetrahedron Lett. 1994 52 9703
41. Donohoe T J., Raoof A, Linney I D., Helliwell M, Org. Lett. 2001 3 861
42. Bolle J, Schneider R, G rardin P, Loubinoux B, Synthesis 1997 1451
43. Tang J, Verkade J, J. Org. Chem. 1994 59 7793
44. Shiraishi H, Nishitani T, Sakaguchi S, Ishii Y, J. Org. Chem. 1998 63 6234
45. Hou D.-R, Hsieh Y.-D, Hsieh Y.-W, Tetrahedron Lett. 2005 46 5927
46. Arnold Z, Holy A, Collect. Czech. Chem. Commun. 1961 26 3059
47. Jana R, Samanta S, Ray J K., Tetrahedron Lett. 2008 49 851
48. Samanta S, Mohapatro H, Jana R, Ray J K., Tetrahedron Lett. 2008 49 7153
49. Jana R, Chatterjee I, Samanta S, Ray J K., Org. Lett. 2008 10 4795
50. Samanta S, Jana R, Ray J K., Tetrahedron Lett. 2009 50 6751
51. Freir a M, Whitehead A J., Tocher D A., Motherwell [nl]W B., Tetrahedron 2004 60 2673
52. Moreno-Ma as M, Pleixats R, Acc. Chem. Res. 2003 36 638
53. Reetz M T., deVries J G., Chem. Commun. 2004 1559
54. Astruc D, Lu F, Aranzaes J R., Angew. Chem. Int. Ed. 2005 44 7852
55. Ranu B C., Chattopadhyay K, Org. Lett. 2007 9 2409
56. Zhang Z, Gan C, Pan C, Zhou Y, Wang Z, Zhou [nl]M.-M, J. Org. Chem. 2006 71 4339
57. Meglla S K., Taylor N J., Rodrigo R, J. Org. Chem. 1992 57 2422
58. General Procedure for the Heck Reaction in Water (Procedure A) b-Bromovinyl aldehyde (1 mmol), Na2CO3 (4 mmol), Bu4NBr (1 mmol), PdCl2 (10 mol%), and H2O (5 mL) were placed in a two-neck round-bottom flask. Methyl acrylate (4mmol) was added, the mixture stirred for 2 h, diluted with aq NH4Cl solution and extracted with Et2O (3 OO25 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and then concentrated. The product was purified by column chromatography using EtOAcb PE as eluent.
59. General Procedure for the Heck Reaction in Acetonitrile (Procedure B) b-Bromovinyl aldehyde (1 mmol), Ph3P (0.25 mmol), Et3N (1.5 mmol), and dry MeCN (5 mL) were placed in a twoneck round-bottom flask fitted with a condenser. The solvent was degassed with N2 and then Pd(OAc)2 (10 mol%) and acrylonitrile (4 mmol) were added. The mixture was heated at 80 B0C for 1 h, cooled; solvent was evaporated, diluted with H2O and extracted with Et2O (3 OO25 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and then concentrated. The product was purified by column chromatography using EtOAcb PE as eluent.
60. General Procedure for the Preparation of Pyrroles To a solution of 3-(2-formyl cycloalkenyl)acrylic ester (0.5mmol) or 3-(2-formyl cycloalkenyl)acrylonitrile (0.5 mmol) in CH2Cl2 (3 mL), amine (0.5 mmol) was added and stirred at r.t. for 5b 30 min. The solvent was evaporated, and then the product was purified by column chromatography using EtOAcb PE as eluent.