Structural elucidation and 1H-NMR, 13C-NMR, and Mass Spectroscopic study of novel 4-chloro-3-formyl-2(vinyl-1-ol) quinolines and 3-formyl-4-hydroxy-2-methyl quinolines

Spectroscopy Letters

Volumn 35, Issue 5, 2002, Pages 741-750

  Kumar, R Nandha ^a   Suresh, T ^a   Mohan, P S ^a  

^a BHARATHIAR UNIVERSITY   (India)

Author keywords

3 Formyl 4 hydroxy 2 methyl quinolines; 4 Chloro 3 formyl 2(vinyl 1 ol)quinolines; 13C NMR; 1H NMR; Mass spectroscopy; Structural elucidation

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; VILSMEIER HAACK REACTION;

EID: 0038071922     PISSN: 00387010     EISSN: None     Source Type: Journal    
DOI: 10.1081/SL-120014944     Document Type: Article

References (19)

1. Meth-Cohn, O.; Stanforth, S.P. In Comprehensive Organic Synthesis; Trost, Fleming, B.M. I., Eds.; Vol. 2, Heathlock, C.H. Vol. Ed.; Pergamon: Oxford, 1991; 777.
2. Ram, S. Singh; Radhey, M. Singh. Synthesis of 4-(N, N-dimethylaminomethylene)-2-alkyl-2-oxazolin-5-ones via Vilsmeier Haack Reagent and their reactions with Various N- and O-nucleophiles. Ind. J. Chem. 2000, 39B, 688-693.
3. A) Meth-Cohn, O.; Bramha Narine. A Versatile New Synthesis of Quinolines, Thienopyridines and Related Fused Pyridines. Tet. Lett. 1978, 23, 2045-2048.
4. B) Khalid, A. Khan; Aboo Shoeb. Chemistry of Carbostyril: Part-I - Oxidation Reactions of 4-hydroxy-1-methyl-2(1H)-quinolines. Ind. J. Chem. 1985, 24B, 62-66.
5. C) Lawrence Bell, H.; Micheal, McGuire; Andrew Freeman, G. Chemistry of 5-pyrimidine carboxyaldehydes. J. Heterocyclic Chem. 1983, 20, 41-44.
6. Tamotsu Fujisawa; Sachio Iida; Toshio Sato. A Convenient Method for the Transformation of Alcohols to Alkyl Chlorides using N, N-Diphenylchlorophenylmethyleniminium Chloride. Chemistry Letters 1984, 27B, 1173-74.
7. Venugopal, M.; Perumal, P.T. A New Method for the Synthesis of Chloroindenes by Vilsmeier reagent. Synth. Comm. 1991, 21, 515-519.
8. Vattoly, J. Majo; Paramasivan, T. Perumal. Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocyles under Vilsmeier Conditions. J. Org. Chem. 1998, 63, 7136-7142.
9. David, R.; Adams; Jose, N. Dominguez; Julio, A. Perez. Synthesis of Quinolines by Reaction of Anilinobutenoates with Vilsmeier Reagent. Tet. Lett. 1983, 24 (5), 517-518.
10. Suresh Chander Roa, M.; Krishna Rao, G.S. Vilsmeier Reaction on some 1-Alkyl-1 laryl allyl alcohols: Benzannulation Heading to Biphenyl-mono & Dicarboxaldehydes. Ind. J. Chem. 1998, 27B, 213-216.
11. Parameswara Reddy, M.; Krishna Rao, G.S. Applications of Vilsmeier Reaction. 13. Vilsmeier Approach to Polycyclic Aromatic Hydrocarbons. J. Org. Chem. 1981, 46, 5371-5373.
12. Alan Katritzky, R.; Charles, M. Marson. Synthesis of a Dodocahydro-18,21-dioxoniakekulene. J. Am. Chem. Soc. 1983, 105, 3279-3283.
13. A) Barnela, S.B.; Seshadri, S. Studies in Vilsmeier-Haack Reaction: Part XIX - Synthesis pf Isoxazolo[3,2-b] quinazolone from 2-hydroxy-3-methyl-4-quinazolone. Ind. J. Chem. 1986, 25B, 709-711.
14. B) Agnes Horvath; Istan Hermecz; Benjamin Podanyi; Zoltan Meszaros. Nitrogen Bridgehead Compounds, Part 50. Vilsmeier-Haack Acylation of 6,7,8,9-Tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones, Part 5. J. Heterocyclic Chem. 1985, 22, 593-599.
15. Nohara, A.; Umetani, T.; Sanno, A. Studies on Antinaphylactic Agents-I: A Facile Synthesis of 4-oxo-4H-1-Benzopyran-3-carboxaldehydes by Vilsmeier Reagents. Tetrahedron 1974, 30, 3553-3561.
16. Egle Beccalli, M.; Alessandro, Marchesina; Henriette, Molanari. The Vilsmeier Reaction with 3,4-Disubstituted Isozaldin-5-ones. A New Synthesis of 1,3-oxazin-6-ones and 1,3-oxazine-2,6-Diones. Tet. Lett., 1986, 27 (5), 627-630.
17. Ram Singh, S.; Radhey Singh, M. Synthesis of 4-(N, N-dimethylaminomethylene)-2-alkyl-2-oxazolin-5-ones via Vilsmeier Haack Reagent and their Reactions with Various N- and O-Nucleophiles. Ind. J. Chem. 2000, 39B, 688-693.
18. Ali Tasneem, M.M.; Rajanna, K.C.; Sai Prakash, P.K. An Efficient and Facile Synthesis of 2-chloro-3-formyl Quinolines from Acetanilides in Micellar Media by Vilsmeier-Haack Cyclisation. Synlett 2001, 2, 251-253.
19. Nandha Kumar, R.; Suresh, T.; Mohan, P.S. Utility of Vilsmeier Haack Reaction: A Novel and Potential Intermediate for the Construction of Newer Nitrogen Heterocycles. Synthetic Communications. 2001 (unpublished results).