An improved synthesis of some 5-substituted indolizines using regiospecific lithiation

Molecules

Volumn 10, Issue 9, 2005, Pages 1074-1083

  Kuznetsov, Alexey G ^a   Bush, Alexander A ^a   Rybakov, Viktor B ^a   Babaev, Eugene V ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

5 benzoylindolizine; 5 formylindolizine; 5 iodoindolizine; 5 lithiumindolizine; Direct lithiation; Oxime; Reduction; Suzuki reaction

Indexed keywords

INDOLIZINE DERIVATIVE; LITHIUM; PROTON;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

INDOLIZINES; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PROTONS; STEREOISOMERISM;

EID: 33644788991     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10091074     Document Type: Conference Paper

References (17)

1. Renard, M.; Gubin, J. Metallation of 2-Phenylindolizine. Tetrahedron Lett. 1992, 33, 4433-4434.
2. Bobrovskii, S. L; Babaev, E. V.; Bundel, Yu. G. Base-promoted deutherium exchange in the indolizine nucleus. Chem. Heterocycl. Comp. (Engl. Transl.) 1987, 9, 1032.
3. Babaev, E. V.; Efimov, A.V. Novel approach to synthesis of indolizine nucleus and the class of 5-aminoindolizines via recyclization of 5-methyloxazolo[3,2-a]pyridinium cation. Chem. Heteroc. Compounds (Engl. Transl.) 1997, 33, 7, 875-876.
4. Yasuyoshi, M.; Toshihiko, Y.; Masazumi, I. A Novel Synthesis of Pyrrolo[2,1,5-de]quinolizinones (Cycl[3.3.2]azinones). Heterocycles 1987, 26, 1, 199.
5. Xin, J.; Ting, H.; Yuefei, H.; Hongwen, H. Novel Synthetic Routes to Nitrogen-Bridged Tricyclic Derivatives of Pyrrolo [2,1,5-cd]indolizine and Pyrrolo[2,1,5-de]quinolizine Derived from 2-Acyl-N-(acylmethyl)pyridinium Halides. J. Chem. Soc. Perkin Trans. I. 2001, 15, 1820.
6. Chichibabin, A. E. Tautomerism in the pyridine series. Chem. Ber. 1927, 60B, 1607-17.
7. Armarego, W. L. F. Ionization and ultraviolet spectra of indolizines. J. Chem. Soc. 1964, 4226-33.
8. Reid, D. H.; Webster, R. G.; McKenzie, S. Studies of heterocyclic compounds. Part 25. Stable indolizine and pyrrolo[2,1-b]thiazole carboselenaldehydes. J. Chem. Soc. Perkin Trans. 1 1979, 2334-9.
9. Babaev, E. V.; Torocheshnikov, V. N.; Bobrovsky, S. I. NMR spectra of indolizines and their sigma-complexes. Chem. Heterocycl. Comp. (Engl. Transl.), 1995, 31, 1079-1087.
10. Babaev E.V., Efimov A.V., Maiboroda D.A. Hetarenes with a nitrogen bridging atom. 1. Phenacylation of 2-substituted 6-methylpyridines. Chem. Heterocycl. Comp. (Engl. Transl.), 1995, 31, 962-968.
11. Babaev, E. V.; Pasichnichenko, K. Yu.; Rybakov, V. B.; Zhukov, S. G., Heterocyclic compounds with a bridge nitrogen atom. 14. Cycloaddition of acetylenedicarboxylic acid ester to 2-chloro-N-phenacylpyridinium ylide. Crystal structure of dimethyl ester of 5-chloro-3-(p-nitrobenzoyl)-indolizine-1,2- dicarboxylic acid. Chem. Heterocycl. Comp. 2000, 36, 1192-1197.
12. Terentyev, P. B., Vinogradova, S. M.; Kost, A. N. Reaction of 2- and 4-vinylpyridines with phenacylpyridinium ylides. Chem. Heterocycl. Comp. (in Russian), 1980, 5, 651-656;
13. [Chemical Abstr. 1980, 93: 220542].
14. Borrows, E. T.; Holland, D. O. Pyrrocolines. V. The action of Grignard reagents and of iodine on 3-acetyl-2-phenylpyrrocoline. J. Chem. Soc. 1947, 670
15. Ogata, K. Heterocyclic compounds. II. Synthesis of indolizine derivatives. Yakugaku Zasshi 1969, 89, 1020
16. Gundersen, L.; Negussie, A. H.; Rise, F.; Oestby, O. B. Antimycobacterial Activity of 1-Substituted Indolizines. Arch. Pharm. 2003, 336, 191.
17. Jones, G.; Sliskovic, D. R. Triazolopyridines. Part 2. Preparation of 7-substituted triazolo[1,5-a]pyridines by directed lithiation. J. Chem. Soc. Perkin Trans. I. 1982, 967.