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Journal of Heterocyclic Chemistry

Volumn 18, Issue 5, 1981, Pages 917-920

Transformations in the 2‐quinolone series

(2) Coppola, Gary M a Hardtmann, Goetz E a

a Sandoz Pharma Ltd (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROQUINOLINE DERIVATIVE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PYRAZOLO[4,3 C]QUINOLINE DERIVATIVE; THEORETICAL STUDY; THIENO[3,2 C]QUINOLINE DERIVATIVE;

EID: 0019781108 PISSN: 0022152X EISSN: 19435193 Source Type: Journal
DOI: 10.1002/jhet.5570180513 Document Type: Article

Times cited : (10)

References (13)

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2
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- Coppola, G.M.¹ Hardtmann, G.E.²

3
- 1542546892
- (1975) Heterocycles , vol.3 , pp. 913
- Mitscher, L.A.¹ Clark, G.W.² Suzuki, T.³ Bathala, M.S.⁴

4
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- (1946) J. Am. Chem. Soc. , vol.68 , pp. 1810
- Lutz, R.E.¹ Codington, J.F.² Rowlett, R.J.³ Deinet, A.J.⁴ Bailey, P.S.⁵

5
- 33947480194
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 4395
- Rapoport, H.¹ Holden, K.G.²

6
- 0343193978
- (1951) J. Am. Chem. Soc. , vol.73 , pp. 2641
- Witkop, B.¹ Patrick, J.P.² Rosenblum, M.³

7
- 37049059876
- J. Chem. Soc.
- (1955) , pp. 4284
- Grundon, M.F.¹ McCorkindale, N.J.² Rodger, M.N.³

8
- 84970560687
- The Infra-Red Spectra of 2- and 4-Quinolones
- (1959) Australian Journal of Chemistry , vol.12 , pp. 589
- Price, J.R.¹ Willis, J.B.²

9
- 37049048664
- J. Chem. Soc.
- (1957) , pp. 2177
- Grundon, M.F.¹ McCorkindale, N.J.²

10
- 76849111383
- (1977) Spectrosc., Letters , vol.10 , pp. 35
- Claret, P.A.¹ Osborn, A.G.²

11
- 84949353427
- N.M.R. Spectral Studies of Some Quinolone Derivatives. Part VII.1Carbon-13 Magnetic Resonance Spectral Studies of N-Methyl-2-Quinolone Derivatives and an Examination ofperiSubstituent Effects
- (1978) Spectroscopy Letters , vol.11 , pp. 351
- Claret, P.A.¹ Osborn, A.G.²

12
- 84985268828
- The product is assumed to have arisen by initial displacement of the chlorine (as observed in compounds 10) by the more basic methylated nitrogen of the methylhydrazine followed by ring closure, although the 2‐methyl isomer, which may form as a result of initial attack at the ester or displacement of the chloring by the unsubstituted nitrogen, cannot be totally discounted. Spectrally, the observed nmr N‐methyl signals (a singlet at δ 4.55 and a singlet at δ 3.95) favor structure 12 as drawn. The methyl group, being colinear with the aromatic ring, would be expected to produce a signal shifted downfield. The isomer 12a would be expected to exhibit both methyl signals closer together. (Formula Presented.)

13
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- Synthesis
- Coppola, G.M.¹ Hardtmann, G.E.²

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