Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
40.8.1.8.2 Variation 2: [3+2] Cycloadditions

DOI: 10.1055/sos-SD-040-00913

Maison, W.Science of Synthesis, (2009401234.

[3+2]-Cycloaddition reactions provide one of the most efficient methods for the synthesis of five-membered heterocycles[‌126‌] and one of the most valuable approaches to 1,2-diazacycloalkanes.[‌127‌,‌128‌]

M-Meeeeeeeeeeeee, e.e. 88, eeeee ee eeeeeeee eeeeeeeeeeee eeee eeeeeeee-eeeeeeeee eeeeeee, e.e. 88, ee eeee eeeeeeeeeeeeeeeee, e.e. 88. Meee eeeeeee eeeeeeee eee eeeee ee Meeeee 88.

Meeeee 88 [8+8] Meeeeeeeeeeeee ee M-Meeeeeeeeeeeee eeee Meeeeeeee Meeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

M8 Me8 Me8 Meeee (%) Mee
M Me 8-MeM8M8 88 [‌888‌]
M 8-eeeee 8-MeMM8M8 88 [‌888‌]
M 8-MMM8M8 8-MeMM8M8 88 [‌888‌]
M 8-MeM8M8 88 [‌888‌]
Me Me Me 88 [‌888‌]

Mee eeeeeeee ee eeeeeeeeee 88 ee eeee-eeeeeeeee eeeeeee 88 eeeeeeee eee eeeeeeee ee eeee ee eeeeee eee eeeeeee 88. Meeeeee eeeeeeee eee eeeee ee Meeeee 88.[‌88‌]

Meeeee 88 [8+8] Meeeeeeeeeeeee ee Meeeeeeeee eeee Meeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

Meeeeeeee 88 Meeeee 88 Meee Meeeeee 88 Meeee (%) Mee
M8MM8, MeMM 88 [‌888‌]
M8MM8, MeMM 888 [‌888‌]
M8MM8, MeMM 888 [‌888‌]
MM8 88 [‌888‌]
MM8 88 [‌888‌]
e MMM8M 888 [‌888‌]
e MeMM 88 [‌888‌]

e Meeeeeeeeeeeee eeeeeeee.

Meeeeeeeeeeeeeee [8+8] eeeeeeeeeeeeee ee eeeeeeeeee 888 eee 888 eeee eeeeeeeee eeeeeee eeee eeee eeee eeeeeeee. Meeeeeeeeeeeee eeeeeeeee ee eeeeeeeeee 888 eeee eeee eeeeee eeee ee 888 eee ee eeeeeeeee eeee eeeeeeeeeeeeee eeeeeee ee eee eeeeee eeeeeee eeeeeeee 888 eeee eeeeeeeee eeeeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee ee eeeee ee Meeeee 88 eee eee eeeeeeeee ee eeeeee eeeeeee 888.[‌888‌] Meeee eeeeeee eee ee eeeeeeeeeee eeee eeeeeeeeeeee eeee ee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeeeeeee eeeeeeeeeee eeeeeee eeee eeeeee eeeeeeeeee 888.

Meeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeee [8+8] eeeeeeeeeeeeee ee eeeeeeeeee 888 eee eeeeeeee ee eeee eeeeeeee eeeeeeeeee 888 eeee eeeeeeeee eeee eeeeee eee eeeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeeeeee eee eeeeee eeeeeeeee eeeeeeeee eeeeeee eeee eeeeeeeeeee 8,8-ee(8-eeeeeeee) (MMMMM) eeeeeeeeeee 888.

Meeeee 88 Meeeeeeeeeeeeeee [8+8] Meeeeeeeeeeeee ee Meeeeeeeee eeee Meeeeee[‌888‌,‌888‌]

Mee 8,8-eeeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeee 888 ee eeeeee eeeeee eeeeeeeeeeeee­eeee 888 ee 888 eee eeee eeeee ee eeee eeee eeeeeee eeeeeee eee eeeeeee.[‌888‌‌888‌,‌888‌‌888‌] Mee eeeeeee eeeeeeee 888 eee ee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeeeee,[‌888‌] eeeeeeee ee eeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee,[‌888‌] ee eeeeeeeeeeeeee ee eeeeeeeeeeeee[‌888‌] {ee. Meeeeee ee Meeeeeeee [Meeeee 88 (Meeeeeeeee Meeeeeeee ee Meeeeeeee eee Meeeeee) Meeeeee 88.88.8.8]}. Meeeeeeeeeeee, eeee eee ee eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeee eeeeeeeeee 888 eeee eeeeeeeee 888 ee eeeee ee Meeeee 88. Meeee eeeeeeeeeeeeee eee eeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeeeee (e.e., eeeeeeeee eeeeeee) eee eeee eee eeeeeee eeeeeeeeeeee 888 ee 888, eeeee eeee eeee eeeeeeeeeeeeeeeeeeee. Meeeeee eeeeeeeee eeeeeeeee 8,8-eeeeeee eeeeeeeeeeeeee ee eeeeeeeeee eeeeee eeeeeeee eeee eeeeeeeee(8)-eeeeeeeee eeeee-eeeeeeee eeeeeeeee eeee eeee eeee eeeeeeee.[‌888‌]

Meeeee 88 8,8-Meeeeee Meeeeeeeeeeeee ee Meeeeeeeee Meeeee eeee Meeeeee ee Meeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

Meeeeee Meeeeee 888 Meeeee ee Meeeee Meeeeeeeeee Meeee (%) Mee
MeMM=MM8 88 [‌888‌]
MeMM=MM8 88 [‌888‌]
MeMM=MM8 88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

8,8-Meeeeee eeeeeeeeeeeeee ee eeeeeeeeee eeeeee 888 ee eeeeeee 888 eee ee eeeeeeeee eeeeeeeeeeeee eeee eeeeee(M) eeeeeeeee ee eeeee ee Meeeee 88. Me eeeeee eeeeeee, eeee ee 888, eee eeeeeeee, eee eeeeeeeee eeeeeeeeeeee 888 eee ee eeeeeeeeeee ee eeee eeeeee eee eeeeeeeeeeeeeeeeeeee.

Meeeee 88 Meeeeeeee Meeeeeeeeeeeeeee 8,8-Meeeeee Meeeeeeeeeeeee ee Meeeeeeeee Meeeee[‌888‌]

Me eeeeeeeeeee eeeeeeeeeee 888 (Meeeee 88), eee M=M eeee ee eeee ee ee eeeeeeee eeee eeeeee. Meeee eeeeeeeeee eee ee eeeeeeeeeeee eeee eeeeee eeeeeee ee eeeeeeeeeeeee ee eeee eeeeeee 888, eeeee eeeee ee 8,8-eeeeeee eeeeeeeeeeeeee eeee eeee eeeeeeee-eeee eee eeeeeeee-eeee eeeeeeeeeeeeee 888 (Meeeeeee'e eeeee MM eeeeeee[‌888‌]) ee eeee eeeeeeeeeeee 888.[‌888‌‌888‌] Me eeeeeeeeeeeeeee eeeeeee eee eeee ee eeeeeeeeeeeeee, eee eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeeeee eeee.

Meeeee 88 8,8-Meeeeee Meeeeeeeeeeeee ee Meeeeeeeee Meeeee[‌888‌‌888‌]

Meeeeeeeeee 88

Meeeee 888 Meeeeeeeeeeee 888 Meeeeeeeeee 888 Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

Meeeeeeeeeeeee 8,8-eeeeeee eeeeeeeeeeeeee eeee eeee eeeee ee ee eeeeee eee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeee, eeeee eee eeeeeeeeee eeeeeeee ee eeeeeee eeeeeee eeeeeeee.[‌888‌‌888‌] Mee eeeeeeeeeeee eee eeeeeeeee ee eeeeeeee eeeeeeeeeee (eeeeeeeeee eeeeeeeee eeeeeee) eee eeee eee eeeeee eeeeeeeee eeeeeeeee eeee eeee eeeeeeeeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeeeee 8,8-Meeeeee Meeeeeeeeeeeee ee Meeeeeee Meeeeeeee Meeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeee 88 (8.88eee) eee eeeeeeeee 88 (8.88eee) eeee eeeeeeeee ee eeeeeee (88eM) eee eeeeeeee eee 8e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeeee eeeee eee eeeeee eeee MeMM (88eM). Mee eeeeeeeee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeee (MeMM).

Meeeeeeee-8M-eeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeeeee ee (M)-8,8,8,8-eeeeeeeee-8,8-ee(8-eeeeeeee) (888, M8,M8=M; 88ee, 8.888eeee) ee MM8Me8 (8.88eM) eee eeeee Me(MMe)8MeMM (8ee, 8.88eeee) ee MM8Me8 (8.8eM) ee ee. Meeee eeeeeeee eee 8.8e, MeMM (8eM, 8.8eeee) ee MM8Me8 (8.88eM) eee eeeee. Meeee e eeeeeee 8.8e, eee eeeeeeeee 888 (8.88eeee) ee MM8Me8 (8.8eM) eee eeeee. Mee eeeeeee eee eeeeeee eeeeeee eee 88e, eee eeee M8M eee eeeee ee eeeeee eee eeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 eee eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee).

8,8-Meeeeeeeeeeeeeeee 888 eee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee eeeeeeee 888 (8eeee), M,M-eeeeeeeeeeeee eeeeeeeee 888 (8eeee), eee eee eeeeeeeeeee eeeeeeeeeeeee (eeeeee ee eeeeee, 8eee) ee eeeee eeeeeee (88eM) eee eeeeeeee eeeee M8 eeeee MMM ee 8M-MMM eeeeeeee eeeeee eee eeeeeee ee eeeeeeee eeeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee.

8,8-Meeeeee-8M,8M-eeeeeeee[8,8-e]eeeeeee-8-eeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeee, e eeee ee MeM (8.8ee, 88 μeee) eee eee eeeeee eeeeee 888 (88 μeee) ee MM8Me8 eee eeeeeee ee ee eee 88eee ee eeeeee eee Me(M)eeeeee eeeeeee. Meee eeee eee eeeee ee e eeee eeeeeeeeee eeeeeeeeee eeeee 888 (8.8eeee) eee Me8MMe (88.8 μM, 8.8eeee), eeee eee eee ee eeeeeeeeee MM8Me8 (8.8eM). M eeee ee eee eeeeee 888 (8.88eeee) ee MM8Me8 (8.8eM) eee eeeee eeeeeeee ee eee eeee eeee 88e, eee eee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88e. Meee eeeeeee eeeeeeeeee eee eeeee eeeeeeeeeee 888 eee eeeeee eeeeeeee eeee e eeeeee eee eeeeee (eeeeeeeeeee eeee Me8M) eee eeeeeeee ee eeeeeeeeeeeeee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee ee e Meeeee Meeeeeeee MM eeeeee (eeeeeee/eMeMM eeeeeeee).

References