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Novel Organic Synthetic Route to Heterocyclic Compounds
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Novel Organic Synthetic Route to Heterocyclic Compounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 March 2024) | Viewed by 17678

Special Issue Editor

Dr. Xinwei He

E-Mail Website
Guest Editor
Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
Interests: multicomponent reaction; transition metal-catalyzed C-H functionalizations; o-AQM chemistry in heterocyclic compound syntheses; novel methodologies development
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue entitled “Novel Organic Synthetic Route to Heterocyclic Compounds” is related to the design and/or development of new strategies for the construction of heterocyclic compounds. Heterocyclic products are important structural units in synthetic and natural products. Among which, structurally diverse polycyclic N- and/or O-containing heterocycles are ubiquitous structural motifs found in bioactive molecules with broad biological properties and functional organic materials. Therefore, novel approaches to the construct the heterocycles have been the subject of intense exploration over the past decade. This Special Issue seeks to highlight the remarkable advancements achieved in the synthesis of heterocycles from activated substrates with multi-reaction sites. It is also our intention for the collection to highlight the remarkable advancements achieved in the heterocyclic compound formation with cutting-edge research articles and state-of-the-art reviews of emerging topics in the field.

Dr. Xinwei He
Guest Editor

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Keywords

  • annulation/cyclization
  • asymmetric catalysis
  • C-H functionalization
  • cascade/tandem reaction
  • green chemistry
  • total synthesis

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Published Papers (11 papers)

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Research

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8 pages, 1840 KiB  
Communication
Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes
by Xueguo Zhang, Jianpeng Zhang, Zhengyi Liu, Wenxuan Bi, Jian Shen and Guang Li
Molecules 2024, 29(9), 2061; https://doi.org/10.3390/molecules29092061 - 29 Apr 2024
Viewed by 761
Abstract
Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction of pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This reaction involved the formation of C–N and C–C bonds and new indolizine compounds with high stereoselectivity [...] Read more.
Herein, we have developed a new approach for the synthesis of indolizine via Cu-catalyzed reaction of pyridine, acetophenone, and nitroolefin under mild conditions in high yields. This reaction involved the formation of C–N and C–C bonds and new indolizine compounds with high stereoselectivity and excellent functional group tolerance. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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16 pages, 1891 KiB  
Article
Iodine-Catalyzed Cascade Annulation of 4-Hydroxycoumarins with Aurones: Access to Spirocyclic Benzofuran–Furocoumarins
by Xuequan Wang, Changhui Yang, Dan Yue, Mingde Xu, Suyue Duan and Xianfu Shen
Molecules 2024, 29(8), 1701; https://doi.org/10.3390/molecules29081701 - 9 Apr 2024
Viewed by 1236
Abstract
An attractive approach for the preparation of spirocyclic benzofuran–furocoumarins has been developed through iodine-catalyzed cascade annulation of 4-hydroxycoumarins with aurones. The reaction involves Michael addition, iodination, and intramolecular nucleophilic substitution in a one-step process, and offers an efficient method for easy access to [...] Read more.
An attractive approach for the preparation of spirocyclic benzofuran–furocoumarins has been developed through iodine-catalyzed cascade annulation of 4-hydroxycoumarins with aurones. The reaction involves Michael addition, iodination, and intramolecular nucleophilic substitution in a one-step process, and offers an efficient method for easy access to a series of valuable spirocyclic benzofuran–furocoumarins in good yields (up to 99%) with excellent stereoselectivity. Moreover, this unprecedented protocol provides several advantages, including readily available materials, an environmentally benign catalyst, a broad substrate scope, and a simple procedure. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Graphical abstract

15 pages, 3267 KiB  
Article
LiOtBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde N-Tosylhydrazones Approach to 3-Substituted 1H-Dibenzo[e,g]indazoles
by Jiaying Lv and Ruimao Hua
Molecules 2023, 28(24), 8061; https://doi.org/10.3390/molecules28248061 - 13 Dec 2023
Cited by 1 | Viewed by 1047
Abstract
A two-step, one-pot synthesis of 3-substituted 1H-dibenzo[e,g]indazoles in good to high yields via a LiOtBu-promoted intramolecular 1,3-dipolar cyclization of 2′-alkynyl-biaryl-2-aldehyde N-tosylhydrazones was developed. The N-Ts-hydrazones used were prepared in situ via the reactions [...] Read more.
A two-step, one-pot synthesis of 3-substituted 1H-dibenzo[e,g]indazoles in good to high yields via a LiOtBu-promoted intramolecular 1,3-dipolar cyclization of 2′-alkynyl-biaryl-2-aldehyde N-tosylhydrazones was developed. The N-Ts-hydrazones used were prepared in situ via the reactions of 2′-alkynyl-biaryl-2-aldehydes and TsNHNH2 (p-methylbenzenesulfonohydrazide). Two types of signals related to the hydrogen bonds, forming in several products, were observed in the 1H NMR spectra recorded in DMSO-d6, assigned to N-H bonds in their dimeric species of product and tautomer. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Figure 1

14 pages, 2079 KiB  
Article
Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes
by Zheng-Guang Wu, Hui Zhang, Chenhui Cao, Chaowu Lu, Aiwei Jiang, Jie He, Qin Zhao and Yanfeng Tang
Molecules 2023, 28(17), 6259; https://doi.org/10.3390/molecules28176259 - 26 Aug 2023
Cited by 1 | Viewed by 1269
Abstract
Developing new organic reactions with excellent atom economy and high selectivity is significant and urgent. Herein, by ingeniously regulating the reaction conditions, highly selective transformations of propargylamines have been successfully implemented. The palladium-catalyzed cyclization of propargylamines generates a series of functionalized quinoline heterocycles, [...] Read more.
Developing new organic reactions with excellent atom economy and high selectivity is significant and urgent. Herein, by ingeniously regulating the reaction conditions, highly selective transformations of propargylamines have been successfully implemented. The palladium-catalyzed cyclization of propargylamines generates a series of functionalized quinoline heterocycles, while the base-promoted isomerization of propargylamines affords diverse 1-azadienes. Both reactions have good functional group tolerance, mild conditions, excellent atom economy and high yields of up to 93%. More importantly, these quinoline heterocycles and 1-azadienes could be flexibly transformed into valuable compounds, illustrating the validity and practicability of the propargylamine-based highly selective reactions. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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14 pages, 1960 KiB  
Communication
Friedel–Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives
by Qi Li, Xiu-Xia Liang, Wang Zhang and Man-Yi Han
Molecules 2023, 28(15), 5685; https://doi.org/10.3390/molecules28155685 - 27 Jul 2023
Cited by 1 | Viewed by 1337
Abstract
A novel double Friedel–Crafts reaction of acylsilanes in water is described. This strategy enables synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. Compared to the 1-silyl-bis(indolyl)methane derivatives from indole substrate, 1-hydroxy-bis(indolyl)methane derivatives were synthesized from the 5-hydroxyindole, [...] Read more.
A novel double Friedel–Crafts reaction of acylsilanes in water is described. This strategy enables synthesis of bis(indolyl)methane derivatives with 1-hydroxy or 1-silyl substituents in moderate to high yield. Compared to the 1-silyl-bis(indolyl)methane derivatives from indole substrate, 1-hydroxy-bis(indolyl)methane derivatives were synthesized from the 5-hydroxyindole, and the hydrogen bonds in the 5-hydroxyindole play a crucial role in regulating the reaction selectivity. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Scheme 1

13 pages, 1929 KiB  
Article
Photoinduced Photocatalyst-Free Cascade Cyclization of Alkynes with Sodium Sulfinates for the Synthesis of Benzothiophenes and Thioflavones
by Hongqiang Dong, Chunli Chen, Jinlei Zhao, Yigang Ji and Wenchao Yang
Molecules 2023, 28(11), 4436; https://doi.org/10.3390/molecules28114436 - 30 May 2023
Viewed by 1649
Abstract
The subject of this investigation is a new method for the construction of sulfonylated heterocycles which overcomes the limitations of classical approaches using a cheap feedstock sulfonylating agent, especially under photocatalyst- and metal-free conditions. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Figure 1

16 pages, 1642 KiB  
Article
Substituent-Controllable Cascade Regioselective Annulation of β-Enaminones with N-Sulfonyl Triazoles for Modular Access to Imidazoles and Pyrroles
by Hua Wang, Tongtong Zhou, Mengdi Wu, Qingqing Ye and Xinwei He
Molecules 2023, 28(11), 4416; https://doi.org/10.3390/molecules28114416 - 29 May 2023
Cited by 1 | Viewed by 1282
Abstract
A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of N-sulfonyl-1,2,3-trizaoles with β-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond to α-imino rhodium carbene, followed by a subsequent intramolecular 1,4-conjugate [...] Read more.
A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of N-sulfonyl-1,2,3-trizaoles with β-enaminones. The imidazole ring was formed through a 1,1-insertion of the N-H bond to α-imino rhodium carbene, followed by a subsequent intramolecular 1,4-conjugate addition. This occurred when the α-carbon atom of the amino group was bearing a methyl group. Additionally, the pyrrole ring was constructed by utilizing a phenyl substituent and undergoing intramolecular nucleophilic addition. The mild conditions, good tolerance towards functional groups, gram-scale synthesis capability, and ability to undergo valuable transformations of the products qualify this unique protocol as an efficient tool for the synthesis of N-heterocycles. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Scheme 1

14 pages, 2512 KiB  
Article
Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Tandem Reaction of C,N-Cyclic Azomethine Imines with α,β-Unsaturated Ketones
by Young Jae Yun and Sung-Gon Kim
Molecules 2023, 28(9), 3710; https://doi.org/10.3390/molecules28093710 - 25 Apr 2023
Cited by 1 | Viewed by 1374
Abstract
An innovative and efficient approach has been developed for the synthesis of 5,6-dihydropyrazolo[5,1-a]isoquinolines. This one-pot tandem reaction involves the reaction of C,N-cyclic azomethine imines with α,β-unsaturated ketones, using K2CO3 as the base and DDQ as [...] Read more.
An innovative and efficient approach has been developed for the synthesis of 5,6-dihydropyrazolo[5,1-a]isoquinolines. This one-pot tandem reaction involves the reaction of C,N-cyclic azomethine imines with α,β-unsaturated ketones, using K2CO3 as the base and DDQ as the oxidant. The process results in functionalized 5,6-dihydropyrazolo[5,1-a]isoquinolines with good yields. This convenient one-step method encompasses a tandem [3 + 2]-cycloaddition, detosylation, and oxidative aromatization. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Scheme 1

15 pages, 2358 KiB  
Article
Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
by Jingya Li, Zhiguo Zhang, Liming Chen, Mengjuan Li, Xingjie Zhang and Guisheng Zhang
Molecules 2023, 28(9), 3691; https://doi.org/10.3390/molecules28093691 - 25 Apr 2023
Viewed by 1893
Abstract
3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of [...] Read more.
3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of alkenes used to deliver conformationally restricted highly substituted aza[3.1.0]bicycles is reported. This reaction was tailor-made for saturated aza[3.1.0] bicycle-containing fused bicyclic compounds that may be applied in the development of concise and divergent total syntheses of bioactive compounds. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Figure 1

20 pages, 1510 KiB  
Article
Acid/Base-Steered Cascade Cyclization: An Efficient One-Pot Access to Diverse Isobenzofuranone and Isoindolobenzoxazinone Derivatives
by Ran Shi, Xiangmin Wang, Xuesi Zhang, Sen Chen, Zu-Li Wang, Huijing Qi and Xin-Ming Xu
Molecules 2023, 28(3), 1443; https://doi.org/10.3390/molecules28031443 - 2 Feb 2023
Cited by 1 | Viewed by 1905
Abstract
We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish [...] Read more.
We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish isobenzofuranone derivatives with high efficiency. However, p-toluenesulfonic acid can promote the product isobenzofuranones to undergo sequential intramolecular rearrangment, nucleophilic addition and cyclization reaction to produce diverse isoindolobenzoxazinones in good yields. The synthetic utility of this method was further demonstrated by the gram-scale preparation of the desired products and the facile transformations of the resulting products. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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Figure 1

Review

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40 pages, 9745 KiB  
Review
Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions
by Zhen-Hua Wang, Yong You, Jian-Qiang Zhao, Yan-Ping Zhang, Jun-Qing Yin and Wei-Cheng Yuan
Molecules 2023, 28(7), 3059; https://doi.org/10.3390/molecules28073059 - 29 Mar 2023
Cited by 6 | Viewed by 3185
Abstract
Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles and have received increasing attention in recent years. In particular, pyridinium and quinolinium 1,4-zwitterions have been widely studied and used in a variety of cyclization reactions due to their [...] Read more.
Heteroarene 1, n-zwitterions are powerful and versatile building blocks in the construction of heterocycles and have received increasing attention in recent years. In particular, pyridinium and quinolinium 1,4-zwitterions have been widely studied and used in a variety of cyclization reactions due to their air stability, ease of use, and high efficiency. Sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions, types of emerging heteroatom-containing synthons, have attracted much attention from chemists. These 1,4-zwitterions, which contain multiple reaction sites, have been successfully used in the synthesis of three- to eight-membered cyclic compounds over the last decade. In this review, we present the exciting progress made in the field of cyclization reactions of sulfur- and nitrogen-based pyridinium and quinolinium 1,4-zwitterions. Moreover, the mechanistic insights, the transition states, some synthetic applications, and the challenges and opportunities are also discussed. We hope to provide an overview for synthetic chemists who are interested in the heterocycle synthesis from cyclization reaction with pyridinium and quinolinium 1,4-zwitterions pyridinium and quinolinium 1,4-zwitterions. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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