Miceller-mediated phosphomolybdic acid: Highly effective reusable catalyst for synthesis of quinoline and its derivatives

Synthetic Communications

Volumn 40, Issue 15, 2010, Pages 2336-2340

  Chaskar, Atul ^a,b   Padalkar, Vikas ^a   Phatangare, Kiran ^a   Langi, Bhushan ^a   Shah, Chetan ^c  

^a C K Thakur Research Centre   (India)

^b POLITECNICO DI MILANO   (Italy)

^c BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Aniline; heteropolyacid; miceller media; quinoline; vinyl aldehydes; vinyl ketones

Indexed keywords

ALPHA,BETA CARBONYL COMPOUND; ANILINE; CARBONYL DERIVATIVE; CROTONALDEHYDE; KETONE DERIVATIVE; METHYLVINYL KETONE; PHOSPHOMOLYBDIC ACID; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICELLE; ONE POT SYNTHESIS;

EID: 77954496870     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903245141     Document Type: Article

References (13)

1. Manske, R. H. F.; Kulka, M. The Skraup synthesis of quinolines. In Organic Reaction; R. Adams (Ed.); Wiley: New York, 1953; vol.7, p. 59.
2. Ozawa, F.; Yanagihara, H. Palladium-catalyzed double carbonylation of aryl halides affording a-keto amides: Applications to synthesis of isatin and quinoline derivatives. J. Org. Chem. 1986, 51, 415.
3. Larock, R. C.; Kero, M. Y. Palladium-catalyzed synthesis of quinolines from allylic alcohols and o-iodoaniline. Tetrahedron Lett. 1991, 32, 569.
4. Larock, R. C.; Babu, S. Synthesis of nitrogen heterocycles via palladium-catalyzed intramolecular cyclization. Tetrahedron Lett. 1987, 28, 5291.
5. Leir, C. M. An improvement in the Doebner-Miller synthesis of quinaldines. J. Org. Chem. 1977, 42, 911.
6. Ranu, B. C.; Allkananda, H.; Jana, U. Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride. Tetrahedron Lett. 2000, 41, 531.
7. Cortese, N. A.; Ziegler, C. B.; Hrnjez, B. J.; Heck, R. F. Palladium-catalyzed synthesis of 2-quinolone derivatives from 2-iodoanilines. J. Org. Chem. 1978, 43, 2952.
8. Diamond, J. E.; Szalkiewicz, A.; Mares, F. Reactions of aniline with olefins catalyzed by group 8 metal complexes: N-Alkylation and heterocycle formation. J. Am. Chem. Soc. 1979, 101, 490.
9. Watanabe, Y.; Shim, S. C.; Mitsudo, T. The rhodium complex-catalyzed synthesis of qui-nolines from aminoarenes and aliphatic aldehydes. Bull. Chem. Soc. Jap. 1981, 54, 3460.
10. Watanabe, Y.; Tsuji, Y.; Suzuki, N. The ruthenium complex-catalysed reductive transformation of nitrobenzene: A novel route to 2,3 dialkylquinolines and N-alkylanilines using saturated alcohols. Chem. Lett. 1981, 1067.
11. Watanabe, Y.; Takegami, Y.; Takatsuki, K. Transformation of o-nitrobenzenes to quino-lines with tetracarbonylhydridoferrate. Bull. Chem. Soc. Jpn. 1978, 51, 3397.
12. Li, X.-G.; Cheng, X.; Zhou, Q. L. A convenient synthesis of 2-alkyl-8-quinoline car-boxylic acids. Synth. Commun. 2002, 32, 2477.
13. Masato, M.; Tabusa, F. Doebner-Miller synthesis in a two-phase system: Practical preparation of quinolines. Tetrahedron Lett. 2000, 41, 8523.