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16.17.6 Addition Reactions to Purine Double Bonds

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (2004161091.

Unlike many other unsaturated heterocycles, purines do not form stable adducts with water. Under photolytic conditions, alcohols react with purine and its riboside (nebularine) by addition across the 1,6-double bond, giving 6-(hydroxyalkyl)-1,6-dihydropurines. Analogous derivatives are obtained from purin-2-amine. When a substituent is already located at the 6-position, the addition occurs at the 7,8-double bond instead. All such adducts are rapidly oxidized in air to the purine. Corresponding additions occur under ionic conditions between hydrosulfite ions and 6-unsubstituted purines having oxo, thioxo, or amino groups at the 2-position.[‌364‌] The resulting moderately stable derivatives are further stabilized by electron-withdrawing substituents at the 8-position. For an overview see ref[‌753‌].

8,8-Meeeeee-8M-eeeee-8-eee (888) eeeeee eeeeeee eeee eeeeee eeeeeee eee eeeeeee ee eeee eee eeeeeeee eeeeee 8,8,8-eeeeeeeee-8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeee-8-eee (888) (Meeeee 888).[‌888‌]

Meeeee 888 8,8,8-Meeeeeeee-8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeee-8-eee ee ee Meeeeeee Meeeeeee ee eee Meeeee Meeeee Meee[‌888‌]

Meeeee (8) eee eee eeeeeeeeeee eeeeeee eeeeeee eeeeeeee ee 8-eeeeeeeeeeeeee eeee eeeeee eee 8,8-eeeeee eeee ee eeee eee 8-(8,8-eeeee-8-eeeeeeeeeeeeeeeeeeeeeeee-8-ee)-8,8-eeeeeee-8M-eeeeeee, e.e. 888 (Meeeee 888).[‌888‌]

Meeeee 888 8-(8,8-Meeee-8-eeeeeeeeeeeeeeeeeeeeeeee-8-ee)-8,8-eeeeeee-8M-eeeeee ee Meeeeeee ee Meeeee eeee 8-Meeeeeeeeeeeee Meee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8,8-Meeeeeeee-8-eeeeee-8,8,8,8-eeeeeeeeee-8M-eeeee-8-eee (888):[‌888‌]

Meeeee eeeeeee (8.888eM, 8.88eeee) eee MeMM (8eM, 88eeee) eeee eeeee ee e eeeeeee ee 8M-eeeee-8-eee eeeeeeeeeeeee (888; 888ee, 8.8eeee) eee eeeee M8MM8 (888ee, 8eeee) ee eee MeMM (88eM). Meeee eeeeeeee eeeee M8 ee ee eee 88e, eee eeeeeee eee eeeeeeee, eee eeeeeeee eee eeeeeeeeee, eee eee eeeeeeee eeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8/MeMM 88:8 ee 8:8) ee eee eeeeeee ee eeee e eeeeeeeee eee; eeeee: 888ee (88%).

8-(8,8-Meeee-8-eeeeeeeeeeeeeeeeeeeeeeee-8-ee)-8,8-eeeeeee-8M-eeeeee (888):[‌888‌]

Meeeee (8; 8.8eeee) eee eeeeeeeee ee M8M (8.88eM) eee e eeeeeeeeeee eeee ee eeeeeeeeeeeeee eeee (8.8eeee) ee M8M (8eM) eee eeeee ee 88°M. Meeeeeee eeeee ee eeee eeeeee eeeeeeeeeee. Mee eeeeeeeeee eee eeeeeeeeeeee eeeeeeeee eee eee eeeeeeee ee eee eeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee eeee M8M; eeeee: 88%; MM (MeMM) λeee (eee ε): 888 (8.88), 888ee (8.88).

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