1949
DOI: 10.1021/ja01180a075
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A New Reaction of Nitriles. III. Amides from Dinitriles

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Cited by 96 publications
(23 citation statements)
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“…The overall yields are slightly lower than the reactions performed in methanol without a Lewis acid. [9] The lower yields could be caused by a known side reaction in which a second isocyanide adds to intermediate 7 (see Scheme 3) [10,5c] or by the possible promotion of other side reactions, such as the Ritter reaction, [11] by the Lewis acid in acetonitrile. A possible explanation for the diastereoselective formation of 2,3-cis pyrrolidines in the Ugi-3C reaction with the -lyxo-pyrroline 2 in the absence of Lewis acids may be found in the existence of an acyloxy intermediate in the course of the reaction (6; X = H, Scheme 3).…”
Section: Resultsmentioning
confidence: 99%
“…The overall yields are slightly lower than the reactions performed in methanol without a Lewis acid. [9] The lower yields could be caused by a known side reaction in which a second isocyanide adds to intermediate 7 (see Scheme 3) [10,5c] or by the possible promotion of other side reactions, such as the Ritter reaction, [11] by the Lewis acid in acetonitrile. A possible explanation for the diastereoselective formation of 2,3-cis pyrrolidines in the Ugi-3C reaction with the -lyxo-pyrroline 2 in the absence of Lewis acids may be found in the existence of an acyloxy intermediate in the course of the reaction (6; X = H, Scheme 3).…”
Section: Resultsmentioning
confidence: 99%
“…Ritter et al reported the direct preparation of amides from nitriles and secondary/tertiary alcohols [1,2] or olefins [3,4] in strong acid medium [5][6][7]. Since the feasibility of the reaction is dependent on the stability of the carbocation formed from the alcohol or olefin during the reaction, application of this method for general practical purposes is limited, although in our laboratory such reactions have been successfully employed in preparing amides and trifluoromethylated amides in good yields [8,9].…”
Section: Introductionmentioning
confidence: 99%
“…Tertiary (equation 15) 45 and benzylic alcohols (equation 16) 46 generally react efficiently, whereas secondary alcohols sometimes undergo rearrangement in conjunction with the Ritter reaction (equation 17). 47 Alternatively, mixtures of standard and rearranged amides can result (equation 18).…”
Section: Chmentioning
confidence: 99%
“…For many years it was believed that primary alcohols did not undergo Ritter reaction at all, 45 but this perceived wisdom now must be revised. Lebedev and Erman 51 (Scheme 14) have obtained good to high yields of amides using methanol, ethanol, or 1-butanol by using reaction temperatures of 100°C or more, and higher molar ratios of alcohol and strong acids relative to the nitrile component.…”
Section: Chmentioning
confidence: 99%