Scope and applicability of an expedient synthesis leading to polysubstituted 3-(carboxyphenyl)pyrroles

Synthetic Communications

Volumn 37, Issue 7, 2007, Pages 1109-1119

  Ullrich, Thomas ^a,c   Ghobrial, Michael ^a   Weigand, Klaus ^a   Marzinzik, Andreas L ^b  

^a Novartis Institutes for BioMedical Research Vienna   (Austria)

^b NOVARTIS PHARMA AG   (Switzerland)

^c Novartis Institutes for Biomedical Research   (Austria)

Author keywords

Chalkones; Feist Benary condensation; Paal Knorr cyclization; Pyrrole synthesis; Stetter reaction

Indexed keywords

ANTIINFLAMMATORY AGENT; PYRROLE DERIVATIVE;

ARTICLE; POLYMERIZATION; SYNTHESIS;

EID: 34147100492     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701198898     Document Type: Article

References (21)

1. Bishop, W. S. 2,5-Dimethylpyrrole derivatives. J. Am. Chem. Soc. 1945, 67, 2261-2262.
2. Paine, J. B. III; Brough, J. R.; Buller, K. K.; Erikson, E. E. Regioselectivity of pyrrole synthesis from diethyl aminomalonate and 1,3-diketones: Further observations. J. Org. Chem. 1987, 52 (18), 3986-3993.
3. Most recent examples include (a) Shi, D.; Shi, C.; Wang, X.; Zhuang, Q.; Tu, S.; Hu, H. An efficient synthesis of substituted pyrroles with the aid of a low-valent titanium reagent. Synlett 2004, 12, 2239-2241;
4. (b) Bharadwaj, A. R.; Scheidt, K. A. Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy. Org. Lett. 2004, 6 (14), 2465-2468;
5. (c) Raghavan, S.; Anuradha, K. Solid-phase synthesis of heterocycles from 1,4-diketone synthons. Synlett 2003, 5, 711-713.
6. (a) Braun, R. U.; Zeitler, K.; Mueller, T. J. J. A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-Knorr sequence. Org. Lett. 2001, 3 (21), 3297-3300;
7. (b) Braun, R. U.; Mueller, T. J. J. Coupling-isomerization-Stetter and coupling-isomerization-Stetter-Paal-Knorr sequences - A multicomponent approach to furans and pyrroles. Synthesis 2004, 14, 2391-2406.
8. (a) Dimmock, J. R.; Jha, A.; Zello, G. A.; Quail, J. W.; Oloo, E. O.; Nienaber, K. H.; Kowalczyk, E. S.; Allen, T. M.; De Santos, C. L.; Clercq, E.; Balzarini, J.; Manavathu, E. K.; Stables, J. P. Cytotoxic. N-[4-(3-aryl-3-oxo-1- propenyl) phenylcarbonyl]-3,5-bis(phenylmethylene)-4-piperidones and related compounds. Eur. J. Med. Chem. 2002, 37 (12), 961-972;
9. (b) Weber, W. M.; Hunsaker, L. A.; Abcouwer, S. F.; Vander Deck, L. M.; Jagt, D. L. Anti-oxidant activities of curcumin and related enones. Bioorg. Med. Chem. 2005, 13 (11), 3811-3820.
10. Stetter, H.; Kuhlmann, H. Addition of aldehydes to activated double bonds, X; Addition of aliphatic, heterocyclic, and aromatic aldehydes to alpha,beta-unsaturated ketones, nitriles, and esters. Chem. Ber. 1976, 109 (8), 2890-2896.
11. Schulte, K. E.; Zinnert, F. Preparation of 1,2,5-substituted pyrroles. Arch. Pharm. 1953, 286, 452-466.
12. Minetto, G.; Raveglia, L. F.; Taddei, M. Microwave-assisted Paal-Knorr reaction. A rapid approach to substituted pyrroles and furans. Org. Lett. 2004, 6 (3), 389-392.
13. Prepared according to Ramos, A. C.; Pelaez, R.; Lopez, J. L.; Caballero, E.; Medarde, M.; San Feliciano, A. S. Heterolignanolides: Furo- and thienoanalogues of podophyllotoxin and thuriferic acid. Tetrahedron 2001, 57 (18), 3963-3978.
14. Medarde, M.; Ramos, A.; Caballero, E.; Pelaez-Lamamie de Clairac, R.; Lopez, J. L.; Gravalos, D. G.; San Feliciano, A. Synthesis and antineoplastic activity of combretastatin analogs: Heterocombretastatins. Eur. J. Med. Chem. 1998, 33 (1), 71-77.
15. Wei, W. G.; Yao, Z. J. A practical procedure for multisubstituted beta-naphthols and their derivatives. Tetrahedron 2003, 59 (34), 6621-6625.
16. Varma, R. S.; Saini, R. K. Solid state dethioacetalization using clayfen. Tetrahedron Lett. 1997, 38 (15), 2623-2624.
17. Ho, T.-L.; Ho, H. C.; Wong, C. M. Dethioacetalization with ceric ammonium nitrate. J. Chem. Soc. Chem. Commun. 1972, 13, 791.
18. Prato, M.; Quintily, U.; Scorrano, G.; Sturaro, A. Cleavage of the 1,3-dithiane protective group. Synthesis 1982, 679-680.
19. Cambie, R. C.; Moratti, S. C.; Rutledge, P. S.; Woodgate, P. D. 1,2-Dibromoethyl acetate, a reagent for Feist-Benary condensations. Synth. Commun. 1990, 20 (13), 1923-1929.
20. Bedoukian, P. Z. Synthesis of bromoacetals. J. Am. Chem. Soc. 1944, 66, 651-652.
21. Verniest, G.; De Kimpe, N. New synthesis of 3-arylpyrroles. Synlett 2003, 13, 2013-2016.