Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

• Kevin Schofield,
• Shayna Maddern,
• Yueteng Zhang,
• Grace E. Mastin,
• Rachel Knight,
• Wei Wang,
• James Galligan and
• Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

• via a deuterated aldehyde is not feasible as deuterium is removed in favor of the aromatic bicyclic product. Both [D2]- and [D1]-isocyanides are exemplified in 7a–c. Finally, we studied the compatibility of the Hantzsch dihydropyridine synthesis with [D1]-aldehydes. The reaction is a condensation of

Oxa-Michael-initiated cascade reactions of levoglucosenone

• Julian Klepp,
• Thomas Bousfield,
• Hugh Cummins,
• Sarah V. A.-M. Legendre,
• Jason E. Camp and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2022, 18, 1457–1462, doi:10.3762/bjoc.18.151

• and not the 1:1 product 6a was the major product (Table 1, entry 1 and Figure 2), presumably due to the equilibria and thermodynamics favoring adduct 5. The Hantzsch dihydropyridine synthesis, and aldol/Michael sequences such as the reaction of hydroxytropolones with aromatic aldehydes give similar

Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions

• Andreas C. Boukis,
• Baptiste Monney and
• Michael A. R. Meier

Beilstein J. Org. Chem. 2017, 13, 54–62, doi:10.3762/bjoc.13.7

• energy consumption and hence lead to more effective and sustainable processes [4][5][6]. MCRs found numerous applications, i.e., in combinatorial chemistry, target oriented synthesis or polymer science [6][7][8]. The most important MCRs are the Strecker amino acid synthesis (1850), the Hantzsch

• dihydropyridine synthesis (1882), the Biginelli dihydropyrimidone synthesis (1891), the Mannich reaction (1912), the Passerini three-component reaction (1921) and the Ugi four-component reaction (1959) [9]. In this work, we used Biginelli and Passerini reactions to synthesize highly functionalized compounds

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• target bond 3-partition dissection maps for 27 commonly found heterocyclic rings is given in the Supporting Information File 1 (see Schemes S6 to S32). These include benzimidazole, 2,3-dihydro-1H-benzo[b][1,4]diazepine, benzofuran, benzopyran, chromen-4-one, coumarin, cyclopent-2-enone, furan, Hantzsch

• dihydropyridine, hydantoin, imidazole, indole, isoquinoline, isoxazole, oxazole, 4H-pyran, pyrazine, pyridazine, pyridine, pyridinone, pyrimidine, pyrimidone, pyrrole, 3H-quinazolin-4-one, quinoline, 1H-quinolin-4-one, and thiophene. For heterocycles that are composed of a fused aromatic ring, such as

The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

• Mrinal K. Bera,
• Moisés Domínguez,
• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

• powerful tools for the assembly of small-molecule libraries [1][2]. MCRs leading to functionalized N-heterocycles [3][4][5][6][7] have long been known before the general concept of MCRs was introduced, e.g. the Hantzsch dihydropyridine synthesis [8] or the Biginelli reaction [9] leading to

A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

• Erli Sugiono and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 2457–2462, doi:10.3762/bjoc.9.284

• optically active tetrahydroquinolines. Readily available substituted 2-aminochalcones were envisioned to undergo photocyclization to the corresponding quinolines which in the presence of a chiral BINOL-derived phosphoric acid diester and Hantzsch dihydropyridine as hydride donor [32][33][34][35][36][37

• programmable syringe pump. The product solution was collected in a flask wrapped with aluminium foil to prevent further irradiation. Our initial investigation of reaction conditions involved the photocyclization–reduction cascade of 2-aminochalcone 1a in the presence of Hantzsch dihydropyridine 4 as hydrogen

• the synthesis of tetrahydroquinolines from readily available 2-aminochalcones using a combination of photochemistry and asymmetric Brønsted acid catalysis. The photocylization and subsequent reduction was performed with catalytic amount of chiral BINOL derived phosphoric acid diester and Hantzsch

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• substituted pyridines is the direct condensation of ammonia (or hydroxylamine) with a corresponding 1,5-diketone. Alternatively, ammonia (or an ammonium salt), an aldehyde and two equivalents of a 1,3-dicarbonyl compound can react via a classical Hantzsch dihydropyridine synthesis. Similarly unsymmetrical

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

• Mark C. Bagley,
• Vincenzo Fusillo,
• Robert L. Jenkins,
• M. Caterina Lubinu and
• Christopher Mason

Beilstein J. Org. Chem. 2013, 9, 1957–1968, doi:10.3762/bjoc.9.232

• Microwave Technology Ltd, 2 Middle Slade, Buckingham, MK18 1WA, UK 10.3762/bjoc.9.232 Abstract The Bohlmann–Rahtz pyridine synthesis and the Hantzsch dihydropyridine synthesis can be carried out in a microwave flow reactor or using a conductive heating flow platform for the continuous processing of

• -substituted propargyl aldehydes undergo Hantzsch dihydropyridine synthesis in preference to Bohlmann–Rahtz reaction in a very high yielding process that is readily transferred to continuous flow processing. Keywords: Bohlmann–Rahtz; continuous flow processing; ethynyl ketones; flow chemistry; Hantzsch

• flow processing, using either microwave dielectric heating or conductive heating, which in this case gave comparable results. Synthesis of dihydropyridines in a continuous flow reactor Introduction to Hantzsch dihydropyridines The Hantzsch dihydropyridine (DHP) synthesis, first discovered in 1881 [61

Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis

• Magnus Rueping,
• Teerawut Bootwicha and
• Erli Sugiono

Beilstein J. Org. Chem. 2012, 8, 300–307, doi:10.3762/bjoc.8.32

• : asymmetric reduction; binolphosphoric acid; Brønsted acid; Hantzsch dihydropyridine; IR spectroscopy; real-time analysis; Introduction In recent years, a growing interest in microreactor technology has been seen in the scientific community and the development of microfabricated reaction systems is actively

• Hantzsch dihydropyridine 2a as hydrogen source and a catalytic amount of chiral Brønsted acid 1a (Scheme 2) [102]. Initial experiments were carried out at 0.1 mL min−1 flow rate in a commercial glass microreactor, which was attached to the ReactIR flow cell for in situ reaction monitoring. In order to