Synthesis of 2-trifluoromethyl thiazoles <i>via</i> [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF<sub>3</sub>CN

Yao, Yunfei; Lin, Bo; Wu, Minze; Zhang, Yafang; Huang, Yangjie; Han, Xijiang; Weng, Zhiqiang

doi:10.1039/d2ob01749k

Cited by 14 publications

(6 citation statements)

References 36 publications

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“…In 2022, Weng's group developed an efficient approach for accessing 2-trifluoromethyl thiazoles 21 (Scheme 4). 26 In the presence of NMP (N-methylpyrrolidone) at 95 °C, the in situ generated Polycyclic nitrogen-containing compounds exist in many natural compounds and drug molecules and show unique biological and pharmacological activities among organic compounds. 27 The construction strategy for polycyclic N-heterocycles has achieved great developments in recent years.…”

Section: Catalyst-free Reactions Of Pyridinium 14-zwitterionsmentioning

confidence: 99%

“…In 2022, Weng's group developed an efficient approach for accessing 2-trifluoromethyl thiazoles 21 (Scheme 4). 26 In the presence of NMP ( N -methylpyrrolidone) at 95 °C, the in situ generated CF 3 CN from 2,2,2-trifluoroacetaldehyde O -(aryl)oxime 20 reacted with pyridinium 1,4-zwitterionic thiolates 1 in a [3 + 2] manner to give 4,5-disubstituted 2-trifluoromethyl thiazoles 21 in good to excellent yields.…”

Section: Cyclization Reactions Of Pyridinium 14-zwitterions and Pyrid...mentioning

confidence: 99%

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Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

2023

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Section: Catalyst-free Reactions Of Pyridinium 14-zwitterionsmentioning

confidence: 99%

“…In 2022, Weng's group developed an efficient approach for accessing 2-trifluoromethyl thiazoles 21 (Scheme 4). 26 In the presence of NMP ( N -methylpyrrolidone) at 95 °C, the in situ generated CF 3 CN from 2,2,2-trifluoroacetaldehyde O -(aryl)oxime 20 reacted with pyridinium 1,4-zwitterionic thiolates 1 in a [3 + 2] manner to give 4,5-disubstituted 2-trifluoromethyl thiazoles 21 in good to excellent yields.…”

Section: Cyclization Reactions Of Pyridinium 14-zwitterions and Pyrid...mentioning

confidence: 99%

Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

2023

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“…More recently, Wen et al investigated the (3 + 2) cycloaddition of pyridinium 1,4-zwitterion with trifluoroacetaldehyde O -(aryl)oxime ( Scheme 9 ) [ 56 ]. The reaction, performed in N -methylpyrrolidone (NMP) at 95 °C, afforded the 2-trifluoromethyl 4,5-disubstituted thiazoles 31 in good-to-perfect yields (30–92% yield).…”

Section: Sulfur-based Pyridinium and Quinolinium 14-zwitterionsmentioning

confidence: 99%

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

et al. 2023

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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.

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“…Therefore, a common strategy utilized to construct trifluoromethyl group‐based energetic materials is to introduce both a trifluoromethyl moiety and detonation groups or rings. Among the fluorine‐containing functional groups used in energetic materials, the trifluoromethyl moiety has been widely reported and explored with extensive theoretical research and investigations regarding its practical applications [89–91] …”

Section: Trifluoromethyl Group Based Energetic Materialsmentioning

confidence: 99%

Fluorine‐Containing Functional Group‐Based Energetic Materials

Guo

Qin

Chen

et al. 2023

The Chemical Record

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Molecules featuring fluorine‐containing functional groups exhibit outstanding properties with high density, low sensitivity, excellent thermal stability, and good energetic performance due to the strong electron‐withdrawing ability and high density of fluorine. Hence, they play a pivotal role in the field of energetic materials. In light of current theoretical and experimental reports, this review systematically focuses on three types of energetic materials possessing fluorine‐containing functional groups F‐ and NF2‐ substituted trinitromethyl groups (C(NO2)2F, C(NO2)2NF2), trifluoromethyl group (CF3), and difluoroamino and pentafluorosulfone groups (NF2, SF5) and investigates the synthetic methods, physicochemical parameters, and energetic properties of each. The incorporation of fluorine‐containing functional moieties is critical for the development of novel high energy density materials, and is rapidly being adopted in the design of energetic materials.

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Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF₃CN

Abstract: A 2,2,2-trifluoroacetaldehyde O-(aryl)oxime was employed for the [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates for the synthesis of 2-trifluoromethyl 4,5-disubstituted thiazoles. The reaction works well with various substituted pyridinium...

Cited by 14 publications

References 36 publications

Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

Fluorine‐Containing Functional Group‐Based Energetic Materials

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Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF3CN

Abstract: A 2,2,2-trifluoroacetaldehyde O-(aryl)oxime was employed for the [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates for the synthesis of 2-trifluoromethyl 4,5-disubstituted thiazoles. The reaction works well with various substituted pyridinium...

Cited by 14 publications

References 36 publications

Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

Recent advances in the cyclization reactions of pyridinium 1,n-zwitterions (n = 4 and 5): scope and mechanism

Recent Progress in Heterocycle Synthesis: Cyclization Reaction with Pyridinium and Quinolinium 1,4-Zwitterions

Fluorine‐Containing Functional Group‐Based Energetic Materials

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Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF₃CN