Definitive structural assignment of condensation products from anthranilamide and 3-amino-2-carbamoylthiophene with ketones. Formation of tetrahydroquinazolinones and their thiophene isosteres

Journal of Heterocyclic Chemistry

Volumn 35, Issue 6, 1998, Pages 1269-1273

  Klemm, LeRoy H ^a   Weakley, Timothy J R ^a   Gilbertson, Robert D ^a   Song, Yang Heon ^b  

^a UNIVERSITY OF OREGON   (United States)

^b Mokwon University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBENZAMIDE; 3 AMINO 2 CARBAMOYLTHIOPHENE; KETONE; TETRAHYDROQUINAZOLINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; CYCLIZATION; DRUG SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032430966     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350605     Document Type: Article

References (21)

1. L. H. Klemm, J. Wang and L. Hawkins, J. Heterocyclic Chem., 32, 1039 (1995).
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3. H. Böhme and H. Böing, Arch. Pharm., 293, 1011 (1960).
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5. J. A. Moore and L. D. Kornreich, Tetrahedron Letters, 1277 (1963).
6. J. Lessel, Arch. Pharm. (Weinheim), 327, 571 (1994).
7. Although we did not attempt to optimize our yields, it appears that the neutral reaction conditions used by Lessel are preferable to our method.
8. However, our nmr data were obtained on a 300 MHz instrument while those of Lessel were obtained on either a 60 or an 80 MHz spectrometer.
9. G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York, NY, 1972, pp 51-54.
10. D. F. Ewing, Org. Magn. Resort., 12, 499 (1979).
11. For example, the calculated chemical shift for C-8a is given by 128.5 (for benzene CH), +19.0 for ipso -NHR, -1.0 for ortho -C(=O)NHR = 146.5 ppm. Thus, the observed signals in 6a-6c and 3 at 147.2 ± 0.4 were assigned to the indicated carbon.
12. J. M. Sanders and B. K. Hunter, Modern NMR Spectroscopy, Oxford University Press, Oxford, UK, 1987, pp 69-75.
13. F. W. Wehrli and T. Wirthlin, Interpretation of Carbon-13 NMR Spectra, Heyden & Son, Inc., Philadelphia, PA, 1980.
14. L. H. Klemm and J. N. Louris, Heterocyclic Commun., 1, 375 (1995).
15. Carrington merely indicated "crystallised from methanol".
16. Reported, colorless plates [3].
17. Consistent with reported characteristics [4].
18. Infrared spectra were determined on samples in potassium bromide wafers by means of a Nicolet Magna IR spectrometer 550; and NMR spectra, (some obtained by Stephen Brand), on samples in hexadeuteriodimethylsulfoxide on a Varian INOVA 300 NMR instrument. Electron impact mass spectra were obtained by Dr. Brian Arbogast of Oregon State University, Corvallis, Oregon, and elemental analyses, by Desert Analytics, Tucson, Arizona.
19. L. J. Bellamy, The Infra-red Spectra of Complex Molecules, 3rd Ed, John Wiley & Sons, New York, NY, 1975, pp 5, 235-246, 281-283.
20. Pulse sequence: relaxation delay one s; pulses 180.0°, 94.7°; acquisition time 0.599 s; spectral width 16501.7 Hz; 736 acquisitions.
21. Same as [21], except for 2784 acquisitions.