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11.17.6.4.3.6.4 Replacement of a Nitrogen Substituent by Hydrogen

DOI: 10.1055/sos-SD-111-00123

Koutentis, P. A.; Ioannidou, H. A., Science of Synthesis Knowledge Updates, (2010) 1, 361.

Thiazol-2-amines ‌218‌ can be protodeaminated via diazotization and subsequent reduction of the diazonium salt (‌Scheme 123‌).[‌157‌,‌439‌-‌441‌]

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‌Meeeeeeeeee 888‌

M8 M8 Meeeeeeeee Meeeee (%) Mee
M e-MeMMM, MMM, 88 °M, 8.8 e 88 [‌888‌]
Me MM8Me MeMM8, M8MM8 e.e. [‌888‌]
8-MMM8M8 MM8Me 8. e-MeMMM, MeMe8, MeMM, 88 °M
8. Me, MeMM, 888 °M		 e.e. [‌888‌]
8-MM8M8 MMMM8 8. MeMM8, M8MM8, 8 °M, 8.8 e
8. Me(M8MM8)8, 8 °M, 8 e		 88 [‌888‌]

e e.e. = eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeee Meeeeee-8-ee-8-[M-(eeeeeeeee)eeeee]eeeeeee [‌888‌, M8 = M(═MMMe)MM8Me; M8 = M]:[‌888‌]

Me e eeee ee eeeeeee-8-eeeee ‌888‌ [M8 = M(═MMMe)MM8Me; M8 = M; 8.88 e, 88 eeee) ee MMM (888 eM) eee eeeee e-MeMMM (8.8 eM, 88.8 eeee) ee MMM (88 eM) eeee 88 eee ee 88 °M. Mee eeeeeee eee eeeeeee eee 8 e ee 88 °M eeeee eee eeeeeeeee eeeeee, eee eee eeee eeeeee eeee e eeeeeee ee MeMMe eee M8M. Mee eeeeeeeee eeeeeee eeeee eee eeeeee eeee M8M eee eeeee, eee eeeee (MeMM8). Meeee eeeeeeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeee) ee eeee ee eeeeeeeee eeeee; eeeee: 8.8 e (88%).

References

[157] Meeeeeee, M.; Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeee. Mee. Meee., (8888) 88, 8888.
[439] Mee, M.-M.; Meeee, M.-M.; Me, M.; Meee, M.-M.; Me, M.-M.; Me, M.-M.; Me, M.; Mee, M.-M., Meeeee. Mee. Meee. Meee., (8888) 88, 8888.
[440] Meeeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeeeee, M. M.; Meeeeeee, M.; Meee, M., M. Mee. Meee., (8888) 88, 8888.
[441] Meeee, M. M.; Meeee, M. M.; Mee, M.; Meee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., Me.; Meee, M.; Meeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meee, M. M.; Mee, M. M. M.; Meeeee, M. M., Meeeee. Mee. Meee. Meee., (8888) 88, 888.

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