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Seela, F.; Ramzaeva, N.; Rosemeyer, H., Science of Synthesis, (2004) 16, 971.
A series of carbocyclic guanine nucleosides is prepared by the general synthetic approach[189–196] starting from 4,6-dichloropyrimidin-2-amine. Firstly, an amine derivative is condensed with 4,6-dichloropyrimidin-2-amine and the resulting 6-chloropyrimidine-2,4-diamine 29 is reacted with 4-chlorobenzenediazonium chloride to afford the 5-(4-chlorophenyldiazenyl)pyrimidine 30. This is reduced with zinc in acetic acid to give the pyrimidinetriamine 31, cyclization of which with triethyl orthoformate gives the chloropurine 32 (Scheme 25).[189–192] The guanosine analogues are obtained by hydrolysis of 32 in dilute aqueous sodium hydroxide.
Meeeee 88 Meeeeeeeeee-Meeeeeeeeee Meeeeeeeeeee Meeeeeeeeee ee Meeeeeeeeee ee Meeeeeeeeeeeeeeeeee eeee Meeee Meeee/Meee Meeeeeee[888–888]
M8 | Meeee (%) ee 88e | Mee |
---|---|---|
88 | [888] | |
88 | [888] | |
88 | [888] | |
88 | [888] |
e Meee 88.
Mee eeeee eeeee/eeee eeeeeee eeeeeeee e eeeeee ee 8-eeeeeeeeeeeeeeee-8,8-eeeeeeee eeee 8-eeeeeeeeeeeee ee eeee eeeee,[888–888] eeeeeeeee eeee eeeeeee ee e eeeee-eeeeeeeeee 8-eeeeeeeeeeeeeeeeeeeeeee, eeeee eee eeeee eeeee ee eeeeeee eeeeeeeee eeee eeeeeeee eeeeeeee (88°M, 8 e) ee eee 8-eeeeeeeeeeee eeeeeeeeeee.[888] Me ee eeeeeeeeee eeee eeeee eee eeee eeeeeeeeee eeee, ee eeeeeeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeee ee eeee eeeee. Me ee eeeeeee eee eee eeeeeeeee ee eeeeee 88 (Meeeee 88).
Meeeee 88 M Meeeee Meeeeeeeee ee Meeeeeeeeee ee e 8-Meeeeeeeeeeeeeeeeeeeeee eeee Meeee Meeee/Meeeeeeeeeee Meee[888]
Meeeeeee eeeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeeee ee ee eeeeeee eeeeeee eeee eeeee eeee ee eeeeeeee eeeeeeeeeee ee eeeeee eeeeeeeee eeee ee 88 eeeeeeee (Meeeee 88).[888,888]
Meeeee 88 Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeeeee eeee Meeeeeee Meeeeeeeeeeeeee[888]
M8 | Meee (e) | Meeee (%) | Mee |
---|---|---|---|
M | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-[8-(Meeeeeeeeeeeeee)eeeeeeee-8-eeee]-8-eeeeee-8M-eeeeee (88):[888]
M eeee ee 8-{[8-(eeeeeeeeeeeeeee)eeeeeeee-8-eeee]eeeee}-8-eeeeeeeeeeeeeee-8-eeeee (888 ee, 8.88 eeee) eee 88 M MMe (888 µM) ee MM(MMe)8 (8.8 eM, 88 eeee) eee eeeeeee eee 8 e ee ee. Mee eeeeeee eee eeeeee eee eeee eeeeee eeee eeee M8M (88 eM). Mee eeeeeee eee eeeeeeeeeee (eM 8–8) ee eeeeeeee ee ee MeMMM8 (∼8 eM), eeeeeeeee eeee MeMMe (8 × 88 eM), eeeee (MeMM8), eeeeeeeeee, eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, 88:8, eeeeeeeeeee/MeMMe 8:8 eee eeee 8:8) ee eeee ee eee eeee eeeeeeeeeeee eeee eeeeeeee ee eeee eeeee eeeeeeee; eeeee: 888 ee (88%); ee 88–88°M.
References
[189] | Meeee, M.; Mee, M., M. Mee. Meee., (8888) 88, 88. |
[190] | Meee, M. M.; Meeeáeeee, M.; Meee, M.; Móeee, M.; Me Meeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 8888. |
[191] | Meee, M.; Meeeee, M. M.; Meeeáeeee, M.; Meee, M.; Móeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[192] | Meeeee, M. M.; Meeeeee, M.; Meeeáeeee, M.; Meeeee-Meee, M.; Meeeeeee, M. M.; Móeee, M.; Meeeeeeee-Meeeee, M. M.; Meeeeeeee, M.; Me Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[193] | Meeeee, M. M.; Meeeeee, M.; Meeeáeeee, M.; Móeee, M.; Meeee, M. M.; Meeeeeeee, M.; Meeeeee, M.; Me Meeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 888. |
[194] | Meeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeáe, M.; Meeeee, M.; Meeeee, M.; Me Meeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 8888. |
[195] | Meeeeeeee, M.; Meee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 8888. |
[196] | Meeeee, M. M. M.; Meeeáeeee, M.; Meeeee, M.; Meeeeeee, M. M.; Móeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Me Meeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 8888. |
[197] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; MeMeee, M. M.; Meee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[198] | Meeeeee-Meeeee, M.-M.; Meee, M., M. Mee. Meee., (8888) 88, 8888. |
[199] | Meeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meee. Meeeeeeeeee. Meeeee., (8888), 888. |
[200] | Meeee, M. M.; Meeeee, M. M.; Meeeeee, M.; Meeeáeeee, M.; Meeeee-Meee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeee, M.; Me Meeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 8888. |
[201] | Meeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M., Meeeeeeeeee Meeeeeeeeee, (8888) 88, 88. |
[202] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M., Meeeeeeeeee, Meeeeeeeeee Meeeeee Meeee, (8888) 88, 888. |
[203] | Meeeeeee, M., M. Meeeeeeeeee. Mee., (8888) 888, 8888. |
[204] | Šeee, M.; Meeáe, M.; Meeöeee, M., Meeeeeeee, (8888), 888. |
[205] | Šeee, M.; Meeáe, M.; Meeöeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.