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Lett."},{"key":"ref28\/cit28c","doi-asserted-by":"crossref","first-page":"3635","DOI":"10.1248\/cpb.34.3635","volume":"34","author":"Kato T.","year":"1986","journal-title":"Chem. Pharm. Bull."},{"key":"ref28\/cit28d","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1248\/cpb.27.183","volume":"27","author":"Matsuda A.","year":"1979","journal-title":"Chem. Pharm. Bull."},{"key":"ref29\/cit29a","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.3987\/COM-07-11014","volume":"71","author":"Dol\u00e1kov\u00e1 P.","year":"2007","journal-title":"Heterocycles"},{"key":"ref29\/cit29b","doi-asserted-by":"crossref","first-page":"58","DOI":"10.3891\/acta.chem.scand.50-0058","volume":"50","author":"Gundersen L.-L.","year":"1996","journal-title":"Acta Chem. Scand."},{"key":"ref29\/cit29c","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1016\/S0040-4020(01)90496-X","volume":"47","author":"Nair V.","year":"1991","journal-title":"Tetrahedron"},{"key":"ref29\/cit29d","doi-asserted-by":"crossref","first-page":"435","DOI":"10.3987\/COM-89-S14","volume":"30","author":"Tanji K.","year":"1990","journal-title":"Heterocycles"},{"key":"ref30\/cit30","unstructured":"The sensitivity of Pd catalysts to excess cyanide is well documented:"},{"key":"ref30\/cit30a","doi-asserted-by":"crossref","first-page":"4828","DOI":"10.1021\/ja078298h","volume":"130","author":"Erhardt S.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30b","doi-asserted-by":"crossref","first-page":"1441","DOI":"10.1016\/j.tetlet.2003.12.040","volume":"45","author":"Chidambaram R.","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref30\/cit30c","doi-asserted-by":"crossref","first-page":"3723","DOI":"10.1021\/ol048643x","volume":"6","author":"Marcantonio K. M.","year":"2004","journal-title":"Org. Lett."},{"key":"ref30\/cit30d","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/S0022-328X(03)00503-5","volume":"684","author":"Sundermeier M.","year":"2003","journal-title":"J. Organomet. Chem."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1248\/cpb.35.72","volume":"35","author":"Hayakawa H.","year":"1987","journal-title":"Chem. Pharm. Bull."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"2385","DOI":"10.1016\/S0040-4039(01)86299-7","author":"C\u00f4ng-Danh N.","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"891","DOI":"10.1081\/NCN-120016613","volume":"21","author":"Gudmundsson K. S.","year":"2002","journal-title":"Nucleosides, Nucleotides Nucleic Acids"},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1080\/07328319708001344","volume":"16","author":"Tu C.","year":"1997","journal-title":"Nucleosides Nucleotides"},{"key":"ref35\/cit35","unstructured":"There are, however, no examples of C(8) purinyl carboxamides where C(2) is substituted with an NR\u2032R\u2032\u2032 group."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"2052","DOI":"10.1248\/cpb.24.2052","volume":"24","author":"Naka T.","year":"1976","journal-title":"Chem. Pharm. Bull."},{"key":"ref37\/cit37","unstructured":"The putative acid formed upon hydrolysis of\n                      1a\n                      readily decarboxylates at room temperature in solution or the solid state; the process can be observed by TLC and\n                      1\n                      H NMR."},{"key":"ref38\/cit38","unstructured":"Also tested was conversion of the carboxylic acid first to its acid chloride (SOCl\n                      2\n                      , 80 \u00b0C, 1 h) and then to the amide (butylamine, NEt\n                      3\n                      , THF, rt). The overall yield for the two-step process was a lower 23%."},{"key":"ref39\/cit39","unstructured":"A comparison of the bond lengths for\n                      1e\n                      ,\n                      1f\n                      ,\n                      2f\n                      ,\n                      3f\n                      , and 2-AP is presented in Table S2 (Supporting Information). The values agree within \u223c0.05 \u00c5."},{"key":"ref40\/cit40","unstructured":"The compound at best only weakly dimerizes in CDCl\n                      3\n                      ; poor solubility at high concentrations (e.g., 10 mM) has prevented a more detailed analysis."},{"key":"ref41\/cit41a","doi-asserted-by":"crossref","first-page":"1589","DOI":"10.1021\/ol0601803","volume":"8","author":"Ong H. C.","year":"2006","journal-title":"Org. Lett."},{"key":"ref41\/cit41b","doi-asserted-by":"crossref","first-page":"18133","DOI":"10.1021\/ja0545517","volume":"127","author":"Park T.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref41\/cit41c","doi-asserted-by":"crossref","first-page":"7636","DOI":"10.1021\/ja00070a007","volume":"115","author":"Nowick J. S.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref42\/cit42a","doi-asserted-by":"crossref","first-page":"688","DOI":"10.1021\/jo040183y","volume":"70","author":"Boiadjiev S. E.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref42\/cit42b","doi-asserted-by":"crossref","first-page":"2032","DOI":"10.1039\/b303879c","volume":"1","author":"Moonen N. N. P.","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"ref43\/cit43a","doi-asserted-by":"crossref","first-page":"8336","DOI":"10.1021\/ja0496367","volume":"126","author":"Yao S.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref43\/cit43b","doi-asserted-by":"crossref","first-page":"9431","DOI":"10.1021\/ja020168f","volume":"124","author":"W\u00fcrthner F.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref43\/cit43c","doi-asserted-by":"crossref","first-page":"1978","DOI":"10.1002\/1521-3773(20000602)39:11<1978::AID-ANIE1978>3.0.CO;2-0","volume":"39","author":"W\u00fcrthner F.","year":"2000","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref44\/cit44a","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/0022-2313(74)90057-X","volume":"8","author":"Smagowicz J.","year":"1974","journal-title":"J. Lumin."},{"key":"ref44\/cit44b","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1111\/j.1751-1097.1966.tb05763.x","volume":"5","author":"Drobnik J.","year":"1966","journal-title":"Photochem. Photobiol."},{"key":"ref44\/cit44c","doi-asserted-by":"crossref","first-page":"2071","DOI":"10.1039\/jr9540002071","author":"Mason S. F.","year":"1954","journal-title":"J. Chem. Soc."},{"key":"ref45\/cit45","unstructured":"The optical behavior of the purines is relatively insensitive to the N(9) substituent. See refs20and14o."},{"key":"ref46\/cit46","unstructured":"For nomenclature, see:"},{"key":"ref46\/cit46a","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1063\/1.1747293","volume":"17","author":"Platt J. R.","year":"1949","journal-title":"J. Chem. Phys."},{"key":"ref47\/cit47","unstructured":"Not discussed here is the n \u2192 \u03c0* (S\n                      0\n                      \u2192 S\n                      2\n                      ) transition that is weak and found at an intermediate energy. See ref14for details."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1111\/j.1751-1097.1993.tb04971.x","volume":"58","author":"Anstead G. M.","year":"1993","journal-title":"Photochem. Photobiol."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1021\/tx0101503","volume":"15","author":"Balu N.","year":"2002","journal-title":"Chem. Res. Toxicol."},{"key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1111\/j.1751-1097.1967.tb08790.x","volume":"6","author":"Eastman J. W.","year":"1967","journal-title":"Photochem. Photobiol."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","unstructured":"Even when a dimethylamino group is at C(6):Albinsson, B.\n                      J. Am. Chem. Soc.\n                      1997\n                      ,119, 6369\u22126375.","DOI":"10.1021\/ja9705203"},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1021\/cr00032a005","volume":"94","author":"Reichardt C.","year":"1994","journal-title":"Chem. Rev."},{"key":"ref53\/cit53a","doi-asserted-by":"crossref","first-page":"2523","DOI":"10.1039\/b707719j","volume":"5","author":"Sinkeldam R. W.","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref53\/cit53b","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1021\/cr020750m","volume":"104","author":"Katritzky A. R.","year":"2004","journal-title":"Chem. Rev."},{"key":"ref53\/cit53c","volume-title":"Solvatochromism","author":"Suppan P.","year":"1997"},{"key":"ref54\/cit54","unstructured":"Specific H-bonding interactions may (ref14o) or may not (refs14band14l) significantly influence 2-AP spectral shifts."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1016\/j.saa.2007.04.016","volume":"69","author":"Mannekutla J. R.","year":"2008","journal-title":"Spectrochim. Acta, Part A"},{"key":"ref56\/cit56","doi-asserted-by":"crossref","DOI":"10.1007\/978-0-387-46312-4","volume-title":"Principles of Fluorescence Spectroscopy","author":"Lakowicz J. R.","year":"2006","edition":"3"},{"key":"ref57\/cit57a","doi-asserted-by":"crossref","first-page":"2739","DOI":"10.1039\/ft9959102739","volume":"91","author":"Ravi M.","year":"1995","journal-title":"J. Chem. Soc., Faraday Trans."},{"key":"ref57\/cit57b","doi-asserted-by":"crossref","first-page":"9133","DOI":"10.1021\/j100088a007","volume":"98","author":"Ravi M.","year":"1994","journal-title":"J. Phys. Chem."},{"key":"ref58\/cit58a","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1002\/jcc.540160312","volume":"16","author":"Wong M. W.","year":"1995","journal-title":"J. Comput. Chem."},{"key":"ref58\/cit58b","doi-asserted-by":"crossref","first-page":"6949","DOI":"10.1021\/j100196a019","volume":"96","author":"Karelson M. M.","year":"1992","journal-title":"J. Phys. Chem."},{"key":"ref58\/cit58c","doi-asserted-by":"crossref","first-page":"4776","DOI":"10.1021\/ja00013a010","volume":"113","author":"Wong M. W.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref58\/cit58d","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1021\/ed047p261","volume":"47","author":"Edward J. T.","year":"1970","journal-title":"J. Chem. Educ."},{"key":"ref60\/cit60","unstructured":"Similar values (within 0.1 \u00c5) come from an alternative equation that does not scale the calculated volume by 1.33, but rather adds 0.5 \u00c5 to the final value of\n                      a\n                      ."},{"key":"ref61\/cit61a","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/0301-0104(96)00184-X","volume":"211","author":"Broo A.","year":"1996","journal-title":"Chem. Phys."},{"key":"ref61\/cit61b","first-page":"1189","volume":"25","author":"Gryczy\u0144ski I.","year":"1977","journal-title":"Bull. Acad. Pol. Sci., Ser. Sci., Math., Astron. Phys."},{"key":"ref62\/cit62a","doi-asserted-by":"crossref","first-page":"946","DOI":"10.1021\/bi001664o","volume":"40","author":"Rachofsky E. L.","year":"2001","journal-title":"Biochemistry"},{"key":"ref62\/cit62b","first-page":"367","volume":"23","author":"Kawski A.","year":"1975","journal-title":"Bull. Acad. Pol. Sci., Ser. Sci., Math., Astron. Phys."},{"key":"ref63\/cit63","unstructured":"Frisch, M. J. T.\u2009et\u2009al.Gaussian, Inc.:Wallingford, CT, 2004."},{"key":"ref64\/cit64","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1023\/A:1008193805436","volume":"14","author":"Schaftenaar G. N., J. H.","year":"2000","journal-title":"J. Comput.-Aided Mol. Design"},{"key":"ref65\/cit65","unstructured":"Data will be reported separately."},{"key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1007\/BF00574445","volume":"42","author":"Ridley J. E.","year":"1976","journal-title":"Theor. Chim. Acta"},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"1031","DOI":"10.1093\/nar\/gki253","volume":"33","author":"Gaied N. B.","year":"2005","journal-title":"Nucleic Acids Res."},{"key":"ref68\/cit68a","doi-asserted-by":"crossref","first-page":"4055","DOI":"10.1093\/nar\/gkm421","volume":"35","author":"Pasternak A.","year":"2007","journal-title":"Nucleic Acids Res."},{"key":"ref68\/cit68b","doi-asserted-by":"crossref","first-page":"4639","DOI":"10.1093\/nar\/25.22.4639","volume":"25","author":"Haaima G.","year":"1997","journal-title":"Nucleic Acids Res."},{"key":"ref68\/cit68c","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/0040-4020(84)85098-X","volume":"40","author":"Gaffney B. L.","year":"1984","journal-title":"Tetrahedron"}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja806348z","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,9]],"date-time":"2023-03-09T14:06:12Z","timestamp":1678370772000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja806348z"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,12,29]]},"references-count":176,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2009,1,21]]}},"alternative-id":["10.1021\/ja806348z"],"URL":"https:\/\/doi.org\/10.1021\/ja806348z","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,12,29]]}}}