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Search for "N-formylation" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
A versatile route towards 6-arylpipecolic acids
Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88
- yield of 88%. (R)-Methyl 6-oxopipecolate (7) was converted under Vilsmeier–Haack conditions [35][40][41] to undergo N-formylation and concomitant enol bromination to give product 2 (Scheme 2). Due to slow degradation of the bromide 2, the subsequent cross-coupling reaction was conducted immediately
- for (2R,6S)-13 and b) for the chair conformations of (2R,6R)-13. ᴅ-2-Aminoadipic acid (1) can be used to generate C6 aryl and alkynyl-modified pipecolic acid derivatives. Methyl ester formation, followed by cyclization, N-formylation, as well as bromination under Vilsmeier–Haack conditions. Suzuki
Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline
Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79
- were crowned by success. In order to completely avoid the possibility of overmethylation [37], the methyl group was introduced by N-formylation of the primary amine group of 25 to give congener 26, followed by reduction of the formyl group with borane–dimethyl sulfide complex [38] to result in
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108
- complete decomposition. With the desired naphthylamines in hand, we were able to complete our synthesis of four chelerythrine variants as shown in Scheme 7. After N-formylation providing intermediates 11 and 12 in good yield, a three-step sequence was performed: Suzuki coupling of the aryl bromide with one
From amines to (form)amides: a simple and successful mechanochemical approach
Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126
- mechanochemical conditions are presented. The two methodologies exhibit complementary features as they enable the derivatization of aliphatic and aromatic amines. Keywords: acetamides; formamides; mechanochemistry; N-formylation; p-tosylimidazole; Introduction The preparation of N-formylated and N-acetylated
- ][50][51][52][53][54], no systematic report of N-formylation and N-acetylation by ball milling has been reported yet. Here, we describe two complementary procedures to prepare formamides and acetamides, applied to primary and secondary aromatic and aliphatic amines. The methodologies directly involve
- outstanding results were achieved in the N-formylation of indoline (Scheme 1, formamide 10). The present methodology could also be effectively applied to the synthesis of N-formylmorpholine (Scheme 1, product 11). Aliphatic primary amines can be more challenging substrates [22]. In fact, when the reaction was
Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93
- intermediate cationic species A and B (Scheme 1), that complicated this reaction. Thus, reaction of amides 1 with benzene and some other arenes in TfOH is an effective way to 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones 2. To show the synthetic potential of dihydroquinolinones 2 their N-formylation and N
- , B under the superelectrophilic activation. N-Formylation and N-acylation of dihydroquinolinones 2. Superelectrophilic activation of the N-formyl group of compounds 5 and their reaction with benzene. Reactions of amides 1a–u with benzene (and other arenes) under superelectrophilic activation, leading
Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics
Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50
- library of acyclic products (Scheme 11), in which the isocyanide input 30 was derived from the corresponding amine via an N-formylation/dehydration sequence [52]. An additional palladium-catalyzed cyclization gave the pyrrolidine mimics 32 in excellent yields and modest to good selectivities (de 8–78
Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker
Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13
- /ethyl acetate (3:2), N-methylation and N-formylation were observed (Supporting Information File 1). Considering prior evidence that methanol can generate formaldehyde in the presence of Pd(0) by an oxidative addition mechanism [43][44] and the observation that apolar solvents cause N-formylation during
Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid
Beilstein J. Org. Chem. 2010, 6, 742–747, doi:10.3762/bjoc.6.93
- 8 with triphenylphosphine in carbon tetrabromide resulted in the bromide 9 [5][6], which was coupled to mercaptopurine 9’ in the presence of sodium hydride in DMF to yield 10 [7][8] in excellent yield. Removal of the N-Troc group with zinc in acetic acid gave intermediate 11 and subsequent N
- -formylation produced 12. Finally, debenzylation with boron tribromide afforded the hybrid molecule 13 as a slightly tan powder [9][10][11][12]. All compounds were fully characterized and their structures confirmed by 1H NMR and mass spectroscopy. The purity of the final product was determined by HPLC and
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