The synthesis of quinoline‐ and isoquinolinecarboxaldehydes
1969; Wiley; Volume: 6; Issue: 2 Linguagem: Inglês
10.1002/jhet.5570060217
ISSN1943-5193
AutoresJ. B. Wommack, T. G. Barbee, David J. Thoennes, Mark A. McDonald, D. E. Pearson,
Tópico(s)Synthesis and biological activity
ResumoJournal of Heterocyclic ChemistryVolume 6, Issue 2 p. 243-245 Note The synthesis of quinoline- and isoquinolinecarboxaldehydes J. B. Wommack, J. B. Wommack Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Post-doctoral student and principal contributor to this research.Search for more papers by this authorT. G. Barbee Jr., T. G. Barbee Jr. Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorD. J. Thoennes, D. J. Thoennes Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorM. A. Mcdonald, M. A. Mcdonald Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorD. E. Pearson, Corresponding Author D. E. Pearson Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203Search for more papers by this author J. B. Wommack, J. B. Wommack Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Post-doctoral student and principal contributor to this research.Search for more papers by this authorT. G. Barbee Jr., T. G. Barbee Jr. Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorD. J. Thoennes, D. J. Thoennes Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorM. A. Mcdonald, M. A. Mcdonald Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203 Pre-doctoral students.Search for more papers by this authorD. E. Pearson, Corresponding Author D. E. Pearson Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37203Search for more papers by this author First published: April 1969 https://doi.org/10.1002/jhet.5570060217Citations: 23 AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat References 5 W. G. Duncan, W. T. Colwell, C. R. Scott, and D. W. Henry, J. Med. Chem., 11, 1221 (1968). 6 The Henry method (5) employs a 4 to 5-fold excess of dimethylsulfonium methylide. In this laboratory, higher yields of heterocyclic epoxides were obtained using 2 equivalents of ylide to I equivalent of aldehyde, more in line with the ratios suggested by E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc., 87, 1353 (1965). 7 S. J. Angyal, Organic Reactions, 8, 210 (1954). Similar to the preparation of o-iodobenzaldehyde from o-iodotoluene. 8 U. M. Rodionov and M. A. Berkengeim, J. Gen. Chem., U.S.S.R., 14, 330 (1944) Chem. Abstr., 39, 4077 (1945). 9 S. J. Angyal, G. B. Barlin, and P. C. Wailes, J. Chem. Soc., 1740 (1953). 10 R. J. Windgassen, Jr., W. H. Saunders, Jr., and V. Boekel-heide, J. Am. Chem. Soc., 81, 1459 (1959) see W. J. Dale, L. Starr and C. W. Strobel, J. Org. Chem., 26, 2225 (1961) for the addition of Grignard reagents to DMF. 11 Melting points were observed with a Thomas Hoover apparatus. Carbon, hydrogen, and nitrogen analyses on all new compounds were done by Galbraith Laboratory and were within 0.2% of the theoretical value except that on 12 which was 0.27% high in carbon. Nmr spectra of all compounds support the assigned structures. Analytical data and nmr spectra are on file. NSF Grant 1683 is acknowledged for the purchase of an nmr spectrometer and NSF-SDP, GU-2057 for the purchase of a mass spectrometer, instruments which greatly aided the research work. 12 F. Richter and G. F. Smith, J. Am. Chem. Soc., 66, 396 (1944). 13 M. Gordon and D. E. Pearson, J. Org. Chem., 29, 329 (1964). 14 N. N. Quang, B. K. Diep and N. P. Buu-Hoi, Rec. Trav. Chim., 83, 1142 (1964). 15 H. Alt, Ann. 252, 318 (1889). 16 J. Kenyon and P. H. Robinson, J. Chem. Soc., 3053 (1926). 17 A. Lachowicz and T. Mazonski, Rozniki Chem., 40, 1849 (1966) Chem. Abstr., 67, 2070 (1967). 18 E. Bamberger, Ann., 441, 297 (1925). 19 Taken in part from the Master's thesis of Mr. Lee H. Davis, Vanderbilt University, 1969. 20 N. P. Buu-Hoi, R. Royer, N. D. Zuong, and P. Jacquignon, J. Org. Chem., 18, 1209 (1953). 21 J. J. Eisch, J. Org. Chem., 27, 1318 (1962). 22 K. Ziegler and H. Zeiser, Ann., 485, 174 (1930). Citing Literature Volume6, Issue2April 1969Pages 243-245 ReferencesRelatedInformation
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