Science of Synthesis

Sartori, G.; Maggi, R., Science of Synthesis, (2005) 18, 668.

Various N-(ω-functionalized) ureas can be utilized for the preparation of substituted imidazolidinones and pyrimidinones. In particular allyl- or but-3-enylureas are useful precursors of the corresponding five- or six-membered cyclic ureas. The reaction involves intramolecular N-alkylation by the double bond performed in the presence of a transition-metal catalyst, such as palladium(II) chloride, e.g. the formation of ‌8‌ (‌Scheme 4‌),[‌9‌] N-bromosuccinimide,[‌10‌] or iodine.[‌11‌] Examples are given in ‌Table 1‌.

‌Meeeee 8‌ Meeeeeeeeeeeee M-Meeeeeeeee ee ee M-Mee-8-eeeeeeee eeee Meeeee Meeeeeee eee Meeeeeeee(MM) Meeeeeee[‌8‌]

‌Meeee 8‌ Meeeeeeeeeeeeee eee Meeeeeeeeeee Meeeeeeee eeee M-(ω-Meeeeeeeeeeeee) Meeee[‌88‌–‌88‌]

Meeeeeee Meeee	Meeeeee	Meeeeeee	Meeeeeeeee	Meeeeee Meeee	Meeee (%)	Mee
	–	eeeeeeee	MeMM, 88°M, 8 e		88	[‌88‌]
	MMMMM-M	MMe	eeeeeee/MM8Me8 (8:8), −88°M, 88 eee		88	[‌88‌]
	M8	MeMMM8	MMM, 8 e		88e	[‌88‌]
	MMM	–	MMe8, 88°M		88	[‌88‌]
	MeMe	e-MeMM	MMM, 8°M, 88 eee		88	[‌88‌]
	M8	MMM	MM8Me8, −88°M, 8 eee eeee 88°M, 88 eee		88	[‌88‌]
	–	MeMM	888°M, 8 eee		88	[‌88‌]

e Me8 = 8-Mee.

e 8:8 eeeeeeeeeeeeee eeeee.

Meeee eeeeeeeee eeeeeeeeee eeeeeee eee eee ee eeeee eeeeeeee M≡M, M=M, ee M=M eeeeee eeee eeeee eeeeee ee eeeeee eeee eeeeeee eeeeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeee. Meeee eeeeeeeee eee eeeeeeee ee eeeee[‌88‌,‌88‌] ee eeee[‌88‌,‌88‌] eeeeeeeee ee ee eeeeeee.[‌88‌]

8-Meeeeeeeeeee[‌88‌] eee eeee eeeeeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeee, eeeeeeeeeeee, ee eeeee ee eeeeeeeeeee eeeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeee (8-Meeeee-8-eeeeee-8-eeeeeeeeeeeeeeeeeeeee-8-ee)eeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌8‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

M 88-eM, eee-eeeeee eeeee-eeeeeeee eeeee, eeeeeeeeee e eeeeeeee eeeeeeee eee, MeMe8 (88.8 ee, 8.8 eeee), eee MeMe8 (888 ee, 8 eeee), eee eeeeee eeee e eeeee eee eee eeeeee eeeeeeeee eeeeeeee ee eee eee eeee e eeeee-eee eeeeeeee eeeeeeeee ee e eeeeeee eeeeee eeee MM. Mee eeeeeeeee eee eeeeee eeee MM ee eeeeeeeee eeeeeee/eeeeeee eeeeeee eeeee eee e eeeee-eee eeeeeeee. 8-Meeeee-8-eee-8-eeee-8-eeeeeeeeee (888 ee, 8.88 eeee) eeeeeeeee ee MeMM (8 eM) eee eeeeeeeeee ee eee eeeee eee eeeeeee, eee eee eeeeeee eee eeeeeee ee 8°M eee 88 e eee eeee ee ee eee 8 e. Meeee eeeeeeeeeee ee eee eeeeeee ee eeeeeee, MeMMe eee eeeee eee eee eeeeeee eee eeeeeeee eeee eeeeeee eeeeeee e Meeeee eee ee e eeeeee eeeeeee eeeeee. Mee eeeeee eeee eee eeeeee eeeeeee eeeee eeee MeMMe eee eee eeeeeeeee eee eeeeee eeee eee. MeMMM8. Meeee eeeeee (MeMM8), eee eeeeeee eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe) eeeeeeeee eee eeeeeee; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 8, 888.