One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• and Heck cyclization reactions. The integration of the multicomponent and post-condensation reactions in one-pot maximizes the pot-, atom-, and step-economy (PASE). Keywords: Heck reaction; one-pot; tetrahydroisoquinoline; tetrazolo-pyrazino[2,1-a]isoquinolin-6(5H)-ones; tetrazole; Ugi-azide reaction

• strategy to develop high pot, atom and step economy (PASE) syntheses [54][55][56][57][58]. We then made the effort to integrate the Ugi and Heck reactions in one-pot for making tetrazolyl-1,2,3,4-tetrahydroisoquinolines 6. Thus, a mixture of 2-bromobenzaldehyde (1a, 1 mmol), allylamine hydrochloride (2, 1

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

• Geng-Xin Liu,
• Xiao-Ting Jie,
• Ge-Jun Niu,
• Li-Sheng Yang,
• Xing-Lin Li,
• Jian Luo and
• Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

• alkene followed by a nucleophilic addition, is unknown (Scheme 1b, bottom). The radical-polar crossover strategy has been steadily emerging in synthetic organic chemistry during the last few years [43][44][45][46]. This strategy allows complex chemicals to be assembled with high step economy that would

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• -pot, and multistep reactions in the synthesis of heterocyclic compounds. The methods have advantages of using readily available starting materials, performing streamlined reactions, producing diverse product structures, and having high pot, atom, and step economy (PASE) [79][80][81] for the diversity

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• are widespread as essential building blocks in various drugs, natural products, agrochemicals, and materials. Modern economy requires developing green strategies with improved efficiency and reduction of waste. Due to its atom and step-economy, the cross-dehydrogenative coupling (CDC) reaction has

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• chemists [79]. Such coupling eliminates the need for prefunctionalization of the substrate, thus making synthetic schemes shorter and more efficient improving the atom and step-economy of the reaction. Other than the clear economic benefits CDC offers, it’s also a facile method for the coupling of sp3 C–H

Me₃Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

• Krishna M. S. Adusumalli,
• Lakshmi N. S. Konidena,
• Hima B. Gandham,
• Krishnaiah Kumari,
• Krishna R. Valluru,
• Satya K. R. Nidasanametla,
• Venkateswara R. Battula and
• Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

• the nitrogen atom of the cyano group into heterocyclic products is still challenging for the synthetic community. In an effort to develop a synthetic strategy for 1-aminoisoquinolines with increased selectivity and step economy by minimizing the generation of byproducts, we hypothesized that if

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• as reduction in waste generation, step-economy, minimum use of solvents, along with atom and bond-forming economy. In addition, MCRs are eco-friendly with simple purification procedures, faster reactions favoring chemo- and regioselectivity in some cases [5][6][7]. The multicomponent strategy has

Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom

• Giovanna Zanella,
• Martina Petrović,
• Dina Scarpi,
• Ernesto G. Occhiato and
• Enrique Gómez-Bengoa

Beilstein J. Org. Chem. 2020, 16, 3059–3068, doi:10.3762/bjoc.16.255

• substrates. Keywords: DFT calculations; gold catalysis; Nazarov reaction; N-heterocycles; Introduction In the development of new and effective catalysts, step economy is surely one of the major goals. A reduction of the number of steps in the synthesis of complex compounds can be attained by cascade

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

• Xiaoming Ma,
• Suzhi Meng,
• Xiaofeng Zhang,
• Qiang Zhang,
• Shenghu Yan,
• Yue Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

• ]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions. Keywords: [3 + 2] cycloaddition; Heck reaction; hexahydropyrrolo[2,1-a]isoquinoline; one-pot reactions

• reactions to make it a green synthetic method with pot, atom and step economy (PASE) [55][56]. Results and Discussion Following the reported procedures for amino ester- and amino acid-based [3 + 2] cycloaddition reactions, pyrrolidine adducts 5 and 6 were synthesized by a three-component reaction of 1 or 2

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

• Liliia Moshniaha,
• Marika Żyła-Karwowska,
• Joanna Cybińska,
• Piotr J. Chmielewski,
• Ludovic Favereau and
• Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

• reductive Ullmann-type chemistry [15], catalytic direct arylations [11][14][16][17], photoinduced cyclodehydrochlorinations [18][19], or nucleophilic oxidative couplings [20], which may offer milder reaction conditions and superior regioselectivities, at the expense of atom and step economy [21]. The latter

Room-temperature Pd/Ag direct arylation enabled by a radical pathway

• Amy L. Mayhugh and
• Christine K. Luscombe

Beilstein J. Org. Chem. 2020, 16, 384–390, doi:10.3762/bjoc.16.36

• growth are the expensive, toxic, and energy-intensive methods in which these materials are typically prepared [1]. Direct arylation is one solution to these problems, which allows improved atom and step economy in polymer synthesis. Traditional coupling methods form a new C–C bond using a reactive C–M

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• renaissance by virtue of its greenness, sustainability, atom economy, step economy and inherent safety. Achieving stereocontrol in such organic electrochemical reactions remains a major synthetic challenge and hence demands great expertise. This review provides a comprehensive discussion of the details of

• organic chemists towards reaching targets selectively from readily available starting materials using low cost, nontoxic reagents and solvents while maintaining high atom and step economy and minimizing waste production with respect to safety standards, electroorganic chemistry (EOC) stands out as a

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• compound were based on the use of prefunctionalized substrates. Instead, the direct trifluoromethylation of C–H bonds of arenes and heteroarenes was a more efficient and ideal protocol due to its atom and step economy. However, the direct trifluoromethylation of C–H bonds was not simple. And only in recent

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• , an aldehyde and an isocyanide proceeds through the isocyanide-involving formal [4 + 1] cycloaddition [39] affording the biologically important imidazo[1,2-a]pyridine scaffold. Due to the atom and step economy, high efficiency and intriguing biological profiles of the products, the GBB reaction has

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• [69] derivatives. The synthesis of thiazoles and their hydrogenated analogues from N-propargylamines offers several advantages, such as high functional group tolerance and high atom and step economy. In continuation of our works [69][70][71][72][73][74], in this review, we will highlight the most

A new and expeditious synthesis of all enantiomerically pure stereoisomers of rosaprostol, an antiulcer drug

• Wiesława Perlikowska,
• Remigiusz Żurawiński and
• Marian Mikołajczyk

Beilstein J. Org. Chem. 2016, 12, 2234–2239, doi:10.3762/bjoc.12.215

• atom and step economy. Since a detailed evaluation of the biological activity and preclinical studies requires gram quantities of each stereoisomer of 1, we sought a shorter and more efficient approach to our targets. Herein we disclose a new total synthesis of all enantiomerically pure rosaprostol

Enantioconvergent catalysis

• Justin T. Mohr,
• Jared T. Moore and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2016, 12, 2038–2045, doi:10.3762/bjoc.12.192

• classical resolution), which generally have a maximum chemical yield of 50%. Enantioconvergent synthesis requires partitioning the synthetic pathway into two distinct sequences, and then merging the materials to the same product and is therefore a compromise in terms of step economy [2]. Despite the

Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp³)–H arylation

• Yunyun Liu,
• Yi Zhang,
• Xiaoji Cao and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2016, 12, 1122–1126, doi:10.3762/bjoc.12.108

• subsequent C–H transformation [10][11][12]. The additional time in running the DG installation reaction and purification as well as related consumption of chemicals substantially undermine the efficiency of the C–H activation-based synthesis, which is against the principle of step economy [13][14]. In this

• known syntheses, a domino process by which the AQ can be linked directly to the raw substrates to enable the subsequent arylation transformation in one pot would be highly favorable for enhancing step economy. Upon this assumption as well as our interest in both domino reactions and C–H

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

• Giorgos Koutoulogenis,
• Nikolaos Kaplaneris and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

• tertiary chiral amine-thioureas, or a combination of catalysts. Products were obtained in one-pot or step-economic domino processes, achieving high increase of molecular complexity in step-economy transformations. There is no doubt that this scientific field will grow in the near future, providing more

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

• Samantha Caputo,
• Andrea Basso,
• Lisa Moni,
• Renata Riva,
• Valeria Rocca and
• Luca Banfi

Beilstein J. Org. Chem. 2016, 12, 139–143, doi:10.3762/bjoc.12.15

• point of view of atom- and step-economy, the use of chiral amines that are retained in the final products will be more valuable [27]. In this case they are not "chiral auxiliaries" and are not removed after the multicomponent reaction, and they contribute to the diversity of the final products. However

Redox active dendronized polystyrenes equipped with peripheral triarylamines

• Toshiki Nokami,
• Naoki Musya,
• Tatsuya Morofuji,
• Keiji Takeda,
• Masahiro Takumi,
• Akihiro Shimizu and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2014, 10, 3097–3103, doi:10.3762/bjoc.10.326

• electrogenerated dendritic diarylcarbenium ions. The simplicity and step economy of this method prompted us to synthesize dendronized polymers equipped with peripheral functional groups by the use of this method. In principle, there are two synthetic approaches for synthesizing peripherally functionalized

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

• Peter H. Huy,
• Julia C. Westphal and
• Ari M. P. Koskinen

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

• targets depicted in Figure 1 and therefore on one relative configuration (either cis- or trans), and have not been proven to be scalable. In our opinion the following examples represent the most efficient synthesis of 3-piperidinols of type B in terms of step-economy (<10 steps to establish the core motif

• (up to 14 g of cis-11a without any purification of intermediates) synthesis of cis- and trans-configured 3-piperidinols 11, which represent a key structural motive in various natural products and other bioactive target compounds. Moreover, a high step-economy (5–6 steps) was guaranteed by several

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

• steps (high step economy). Keywords: alicyclic; bisallenes; cyclic; cycloadditions; cycloisomerization; isomerization; molecular complexity; step economy; Table of Contents Introduction Review Acyclic conjugated bisallenes 1.1 Synthesis of hydrocarbons 1.2 Synthesis of functionalized systems 1.3

Multicomponent reaction access to complex quinolines via oxidation of the Povarov adducts

• Esther Vicente-García,
• Rosario Ramón,
• Sara Preciado and
• Rodolfo Lavilla

Beilstein J. Org. Chem. 2011, 7, 980–987, doi:10.3762/bjoc.7.110

• ideal reaction, such as atom- and step economy, convergence, and exploratory power, together with new avenues in connectivity, leading to the straightforward synthesis of previously unobtainable scaffolds [3]. In this context, it is possible to obtain a wide variety of complex tetrahydroquinolines

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

• Da Xu,
• Michael A. Drahl and
• Lawrence J. Williams

Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104

• pluripotent route that would enable direct access to a broad range of these targets would be useful and would offer advantages over single-target routes, especially in terms of overall step economy. Given the difficulties associated with the stereoselective preparation of endocyclic allenes, and the fact that