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16.17.3.3.2.3 Variation 3: By Bromination

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (2004161007.

8-Bromopurines 121 and their nucleosides can be obtained in a one-pot reaction by treatment of the corresponding precursors with bromine or N-bromoamides. If the substrate contains alkyl groups, then side-chain bromination is possible with most bromination reagents including bromine or N-bromosuccinimide. As side-chain halogenation is catalyzed by light, the reactions should be run in the absence of light whenever possible.

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MM MM8 Me M8M, ee, 8e 88 [‌888‌]
MM MM8 MM8M(MM8)8MM M8M, 8°M, 8e 88 [‌888‌]
MM MM8 8-eeeee-β-M-eeeeeeeeeeeee M8M, ee 88 [‌888‌]
MM MM8 8,8,8-eee-M-eeeeee-β-M-eeeeeeeeeeeee MeMM, MeMMe, 88°M, 8e 88 [‌888‌]
MM8 M 8,8,8-eee-M-eeeeee-β-M-eeeeeeeeeeeee MeMM, MeMMe, 88°M, 88e 88 [‌888‌]
MM8 M 8-eeeee-β-M-eeeeeeeeeeeee MeMMe, MeMM, M8M, eM8.8, ee, 8.8e 88 [‌888‌]
MM8 MM β-M-eeeeeeeeeeeee MeMM, MeMMe, ee, 8e 88 [‌888‌]
MM8 MM8 (MM8)8MMM8M(M)(MeMe)8 MMM, MMe8, ee, eeeeeeeee 88 [‌888‌]
MMMe M M 888°M, 8e 88 [‌888‌]
MMe8 M Me 8.8M MeMMe, ee, 8e 88 [‌888‌]

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Meeeeee eeeeeeeeeee ee 8-eeeee-8-(eeeeeeeeeeee)-8-(eeeeeeeeeeeeeee)eeeeee 888 eee eeeeeeeeeee ee eeeeeeee ee eee eeeee eeee M-eeeeeeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee ee Meeeeee eeee M-Meeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee (888, M8=MM8; M8=MM; M8=β-M-Meeeeeeeeeeee):[‌888‌]

Me e eeeeeeeeee ee eeeeeeeeeeee (888ee, 8.8eeee) ee eeeeeee MeMM (88eM) eeeeeeeeee eeeee MeMMe (888ee, 8eeee) eee eeeee eeee 8e Me8 (888ee, 8eeee) ee MeMM (8eM). Mee eeeeeee eee eeeeeee ee ee eee 8e eee eeee eeeeeeeeee ee eeeeeee eee eeeeeeeee eeee eeeeeee/MeMM (8×). Mee eeeeeee eee eeeeeee eeee e eeeee eeeeee ee M8M eee eeeeeeeeeeeeeeeeeee eeee eeeeeeee eee eeeeeeee; eeeee: 888ee (88%); ee >888°M.

8-Meeee-8-(β-M-eeeeeeeeeeeee)-8M-eeeeee-8,8-eeeeeee (888):[‌888‌]

M eeeeeeeeee ee 8-(β-M-eeeeeeeeeeeee)-8M-eeeeee-8,8-eeeeeee (888ee, 8.88eeee) eee MMM (888ee, 8.88eeee) ee M8M (8.8eM) eee eeeeeee ee ee eee 8eee. Mee eeeeeee eee eeeeeee ee eeeee, eee eee eeeee eeeeeee eee eeeeeeeeeeeeeee (MM8Me8/MeMM 8:8); eeeee: 888ee (88%); ee 888°M.

References


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