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1.2.1.7.4 Reaction of Salicylaldehyde and Derivatives

DOI: 10.1055/sos-SD-210-00137

Carboni, B.; Berrée, F.Science of Synthesis: Multicomponent Reactions, (20141240.

A novel approach to functionalized 2-[(dialkylamino)methyl]phenols 26, which are attractive structures for the development of pharmaceuticals and agrochemicals, has been developed by Petasis[‌81‌] in parallel with work by other groups.[‌82‌] The procedure involves the one-pot reaction of a boronic acid, an amine, and a salicylaldehyde, and is found to be more general with secondary amines while primary amines afford the expected products in modest yields (Scheme 24). Modifications of the experimental conditions (use of microwave irradiation or molecular sieves, solvent-free conditions, or the use of ionic liquids or water as the solvent) have been used to accelerate the borono-Mannich condensation, increase conversion and yield, and facilitate purification.[‌11‌,‌26‌,‌83‌‌87‌]

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M8 M8 M8 M8 M8 Meeeeeeeee Meeeee (%) Mee
Me Me M M MeMM, ee, 88 e 88 [‌88‌]
Me Me M MM8 MeMM, ee, 88 e 88 [‌88‌]
Me Me (M)-MMMMMe M M MeMM, ee, 88 e 88 [‌88‌]
Me Me 8-MeMM8M8 M MM8 MeMM, ee, 88 e 88 [‌88‌]
Me Me 8-MeMM8M8 M M M8M, 88 °M, 88 e 88 [‌88‌]
Me Me 8-eeeee M M MeMM, ee, 88 e 88 [‌88‌]
Me M 8-eeeee M M MeMM, ee, 88 e 88 [‌88‌]
Me Me 8-Mee M M M8M, 88 °M, 88 e 88 [‌88‌]
MM8MMMM8 MM8MMMM8 Me M M M8M, 88 °M, 88 e 88 [‌88‌]
(MM8)8MMee(MM8)8 8-MeMM8M8 M Me MeMM, ee, 88 e 88 [‌88‌]
(MM8)8M(MM8)8 (M)-MMMMMe M M MeMM, ee, 88 e 88 [‌88‌]
(MM8)8M(MM8)8 Me M M eeeeeee, 88 °M, 88 e 88e [‌88‌]
(MM8)8M(MM8)8 Me MM M eeeeeee, 88 °M, 88 e 88e [‌88‌]
(MM8)8 8-Mee M M M8M, 88 °M, 88 e 88 [‌88‌]

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Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meeeee (%) Mee
Me Me Me M M 88 [‌88‌]
Me Me Me M MM8 88 [‌88‌]
Me Me Me M M 88 [‌88‌]
(MM8)8M(MM8)8 Me Me M 88 [‌88‌]
(MM8)8M(MM8)8 Me M Me 88 [‌88‌]
(MM8)8M(MM8)8 8-Mee M MM8 88 [‌88‌]
(MM8)8M(MM8)8 e-Me M M 88 [‌88‌]

e Meeee ee eeeeeeee eeeeeee.

Mee eeeeeeeeee ee eeee eeeeee-Meeeeee eeeeeeee eee eeee eeeeeeee ee eee eeeeee eeeeeeeeeee ee 8M-8-eeeeeeeeeee 88 ee eeeeeeeee eeeeee. Meeeeee, eee eeeeeeee eeeeee ee eeeeeeeeee e eeee eeeeeeeeeeeeee eeeeeee eeeeeee eee eeeee eeee eeee eee eeeeee ee eee eeeee eeeeeeee. Mee eeeeeeee eeeeeeeeee eeeeeee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeee eeee eeeeeeeeeeeeee eeeee eee eeeeeeeeeeeee (8 eee%) ee eeeeeee ee 88 °M (Meeeee 88);[‌88‌] eeeeeee, eeee eeeeee eee eeee eeeeeeeeeeee ee eeee eeeeee eee eeeee eeeeeeee eeeeeeeeee eeee eeee eeeeeeeeee, eeeeeeeee eee eee ee eeeeeeee eeeeee eee eeeeee eeeeeeee eeee ee eeeee eee eeeeeee.[‌88‌,‌88‌,‌88‌]

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Meeeeeeeeee 88

M8 M8 M8 M8 M Meeee (Meeee) Meeeeeeeee Meeee (%) Mee
Me Me M M M(MM)8 8.88 eeeeeee, 88 °M, 88 e 88 [‌88‌]
Me Me Me M M(MM)8 8 M8M, 88 °M, 8 e 88 [‌88‌]
Me Me M Me M(MM)8 8.8 M8M, 88 °M, 88 e 88 [‌88‌]
Me Me M M M(MM)8 8.8 M8M, 88 °M, 88 e 88 [‌88‌]
Me Me Me M MM8M 8.8 MMM, 88 °M, 88 e 88 [‌88‌]
Me Me MM8 M MM8M 8.8 MMM, 88 °M, 88 e 88 [‌88‌]
Me M MM8 M MM8M 8.8 MMM, 88 °M, 88 e 88 [‌88‌]
Me (MM8)8Me MM8 M MM8M 8.8 MMM, 88 °M, 88 e 88 [‌88‌]

Mee eeeeeeeeee eeeeeeeee eeeeeeee, eeeee eeeeeeeee eeeeeee eeeeeeeee, eee eeeeeeeeeeee ee eee eeeeeeeee eeeeee ee eee eeeeeee eeee, eee eeeeeeeeeeeeee eeeeeeee ee eee eeeeeee eeeee. Meee ee eeeeeeee ee eeeeee eeeeeeeeeee ee ee eeeeeeee eeeeeee eeeee ee ee eeeeeeeeeeeee eeee eeeeeee ee eeee eee eeeeeee (Meeeee 88).[‌88‌,‌88‌,‌88‌] Me eeeeeeeee eeeeeeeeeeee eeeeeeee eeeeeee 8-eeeeeeeeeeeeeeeeeeeeeeee eee eeeeeee(eeeeeeeee)eeeeeee ee eeeeeee ee e eeeeeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeee eeeeeeeeeee.[‌88‌]

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8-[(Meeeeeeeeeee)eeeeee]eeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

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8-Meeee-8M-8-eeeeeeeeee (88, M8 = Me; M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeeeeeeeee (88 ee, 8.8 eeee), (M)-eee-8-eeeeeeeeeee eeee (88 ee, 8.8 eeee), eee Me8MM (8 ee, 8.888 eeee, 8 eee%) ee eeeeeee (8.8 eM) eee eeeeeee ee 88 °M eee 88 e (eeeeeeeee) eee eeee eeeeeee ee eeee ee ee. M8M (88 eM) eee MM8Me8 (88 eM) eeee eeee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee 88% MMe eee eee. ee MeMMM8, eeeee, eee eeeeeeeeeeee ee eeeeee eee eeeeeee ee e eeeee eeeeeee; eeeee eeeee: 88 ee (88%). Meeeeee eeeeeeeeeeee eee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8).

References