Reference

Synthesis of novel 2-aryl AICAR derivatives

Synthesis of novel 2-aryl AICAR derivatives. Kohyama, Naoki; Katashima, Tomoyuki; Yamamoto, Yukio (Graduate School of Human & Environmental Studies, Kyoto University, Kyoto 606-8501, Japan). Synthesis, (17), 2799-2804 (English) 2004 Georg Thieme Verlag. CODEN: SYNTBF. 6783-05-7 and 5720-07-0 which are cas registry numbers are also used here. ISSN: 0039-7881. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) Novel 2-aryl AICAR (5-Amino-1-b-D-ribofuranosylimidazole-4-carboxamide) derivs. were synthesized via the Suzuki-Miyaura cross-coupling reactions of 8-bromoadenosine. Following conversion of the adenine moiety to hypoxanthine and the introduction of a MEM group, hydrolysis gave desired 2-aryl AICAR derivs. .

Dihalogenation of N,O-disubstituted hydroxypyridones and use of the products in the organopalladium-catalyzed coupling reactions

All Rights Reserved. Dihalogenation of N,O-disubstituted hydroxypyridones and use of the products in the organopalladium-catalyzed coupling reactions. Balme, Genevieve; Conreaux, David; Monteiro, Nuno; Bossharth, Emmanuel; Desbordes, Philippe (Bayer CropScience SA; Centre National de la Recherche Scientifique, Fr.). PCT Int. Appl. WO 2007006591 A2 18 Jan 2007, 36pp. DESIGNATED STATES: W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC; RW: AT, BE, BF, BJ, CF, CG, CH, CI, CM, CY, DE, DK, ES, FI, FR, GA, GB, GR, IE, IS, IT, LU, MC, ML, MR, NE, NL, PT, SE, SN, TD, TG, TR. (French). (World Intellectual Property Organization). CODEN: PIXXD2. CLASS: ICM: C07D. APPLICATION: WO 2006-EP9181 12 Jul 2006. PRIORITY: EP 2005-356121 13 Jul 2005. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 5, 63 The invention is related to the prepn. of (non)sym. N,O-disubstituted 3,5-dihalo-4-hydroxypyridin-2(1H)-ones I [X1, X2 = independently Cl, Br, I; R1 = haloalkyl, alkylcarbonyl, carbamoyl, etc.; R2 = cyclo/cyano/alkyl, formyl, etc.; R3 = H, halo/cyclo/alkyl, etc.] and their salts that are useful intermediates in the synthesis of compds. 516-12-1 and 5720-07-0 are also in the experiment. with agrochem. or pharmaceutical activity by stepwise halogenation or one-pot dihalogenation at the 3 and 5 positions of the coresponding 4-hydroxypyridin-2(1H)-ones with a halogen superelectrophile generated by the action of 32 equiv of halogen donor compd. in the presence of a (non)catalytical amt. of a strong acid and optionally an org. solvent. The invention is also related to the use of dihalogenated hydroxypyridones I in coupling reactions catalyzed by organometallic, particularly organopalladium, compds. Thus, iodination of 4-methoxy-1-methylpyridin-2(1H)-one with NIS in acetonitrile in the presence of TFA at room temp. for 3 h gave 3,5-Diiodo-4-methoxy-1-methylpyridin-2(1H)-one (II; m.p = 134°). Coupling of diiodide II with 4-methoxyphenylboronic acid in the presence of dichlorobis(triphenylphosphine)palladium(II) gave 4-methoxy-3,5-bis(4-methoxyphenyl)-1-methylpyridin-2(1H)-one. .