Organic Chemistry Portal >
Reactions > Organic Synthesis Search

Categories: C-N Bond Formation > Synthesis of substituted N-heterocycles >




Recent Literature

In ionic liquids [Bmim][PF6] or [Bmim][BF4], a highly regioselective N-substitution of pyrrole with alkyl halides, sulfonyl chlorides, and benzoyl chloride gave substituted pyrroles in excellent yields. Michael addition of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford N-alkylpyrroles.
Z.-G. Lea, Z.-C. Chen, Y. Hu, Q.-G. Zheng Synthesis, 2004, 1951-1954.

In an electrochemical method for the selective N1-acylation of indazoles, indazoles are reduced to indazole anions and H2. A subsequent reaction with acid anhydrides results in selective acylation of the N1-position. This procedure can also be applied to the acylation of benzimidazoles and indoles.
D. M. M. M. Dissanayake, A. J. Vannucci, Org. Lett., 2019, 21, 457-460.

An improved one-pot procedure for the preparation of N-acylbenzotriazoles involves mild reaction conditions and allows the preparation of several derivatives not accessible by the previously reported methods.
A. R. Katritzky, N. Kirichenko, B. V. Rogovoy, Synthesis, 2003, 2777-2780.

Readily available N-acylbenzotriazoles efficiently acylate aqueous ammonia and primary and secondary amines to give primary, secondary, and tertiary amides in very good yields.
A. R. Katritzky, H.-Y. He, K. Suzuki, J. Org. Chem., 2000, 65, 8210-8213.

A convenient reaction of carboxylic acids with 1H-benzotriazole provides N-acylbenzotriazoles in good yields in the presence of only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh3.
M. Singh, A. S. Singh, N. Mishra, A. K. Agrahari, V. K. Tiwari, Synthesis, 2019, 51, 2183-2190.

The combination of 2,2′-dipyridyl disulfide and PPh3 enables the conversion of carboxylic acids into the corresponding N-acylbenzotriazoles in the presence of 1H-benzotriazole. This base-free reaction offers mild conditions, short reaction time, and wide substrate scope.
A. S. Singh, A. K. Agrahari, N. Mishra, M. Singh, V. K. Tiwari, Synthesis, 2019, 51, 470-476.