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CAS indexed 70 chemical substances from this document.
CAS subject entries for this document include: Cycloaddition reaction; Human; Blood plasma; and 3 additional concepts. | |
CAPLUS COPYRIGHT 2004 ACS on STN
| TITLE:
| Process for preparation of 1,4-disubstituted [1,2,3]-triazoles by metal-catalyzed, in particular copper-catalyzed, regioselective Huisgen 1,3-dipolar cycloaddition of azides and acetylenes |
| INVENTOR(S):
| Sharpless, Barry K.; Fokin, Valery; Rostovsev, Vsevolod; Green, Luke; Himo, Fahmi |
| PATENT ASSIGNEE(S):
| The Scripps Research Institute, USA |
| SOURCE:
| PCT Int. Appl., 34 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- --------------- --------
WO 2003101972 A1 20031211 WO 2003-US17311 20030530
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN,
CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH,
PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ,
UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW, AM, AZ, BY, KG, KZ, MD,
RU, TJ, TM
RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AT, BE, BG,
CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC,
NL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ,
GW, ML, MR, NE, SN, TD, TG
ABSTRACT:
The invention is directed to a process for Huisgen 1,3-dipolar cycloaddn. of azides and terminal acetylenes for forming 1,4-disubstituted [1,2,3]-triazoles regioselectively, catalyzed by the addn. of Cu(II) in the presence of a reducing agent, for reducing Cu(II) to Cu(I), in situ, in catalytic amt. The invention also discloses the use of aq. Cu(I) solns. and other metals such as Au, Ag, Hg, Cd, Pt and Pd. The advantages include lower reaction temps., even room temp., high regioselectivity, use of the cheaper and purer Cu(II) salts, and no functional group interference. For instance, I was prepd., in 94% yield, by Huisgen 1,3-dipolar cycloaddn. of 17-ethynyl estradiol and (S)-3-azidopropane-1,2-diol in the presence of 1 mol% CuSO4.bul.5H2O and 10 mol% sodium ascorbate in water/t-BuOH mixt. at room temp. overnight.
Updated 5/4/2007 7:42:59 AM
