ChemInform Abstract: Domino Aziridine Ring Opening and Buchwald—Hartwig Type Coupling‐Cyclization by Palladium Catalyst.

Rao, R. Koteshwar; Karthikeyan, Iyyanar; Sekar, Govindasamy

doi:10.1002/chin.201310184

Cited by 3 publications

(3 citation statements)

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“…Recently, Sekar and co-workers revisited their synthetic route towards 1,4-benzoxazine derivatives from activated aziridines and succeeded to generalize the strategy further by employing inexpensive 2-bromo-and 2-chlorophenols using palladium catalyst [213]. To achieve this, when various cycloalkane-fused and 2-phenyl-N-tosylaziridines (367, 374, 491a, 8) were reacted with 2-bromo-and 2-chlorophenols 523 in the presence of 5 mol% Pd 2 (dba) 3 , 10 mol% ligand (AE)-BINAP, and 2.0 equiv.…”

Section: Synthesis Of Six-membered Rings From Activated Aziridines Anmentioning

confidence: 98%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

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Section: Synthesis Of Six-membered Rings From Activated Aziridines Anmentioning

confidence: 98%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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“…The investigation of the potential of eucalyptol as a solvent in Buchwald-Hartwig coupling began with a literature review to determine the best conditions for this type of transformation [132][133][134][135][136][137][138][139][140][141][142][143][144]. After compiling the main and most widely used reaction conditions for this coupling, the authors chose the conditions that were mainly applicable to the heterocycles frequently used by their team.…”

Section: Buchwald-hartwig Coupling Reactionmentioning

confidence: 99%

Eucalyptol, an All-Purpose Product

Campos

Berteina‐Raboin

2022

Catalysts

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Eucalyptus plants have attracted the attention of researchers and environmentalists worldwide because they are a rapidly growing source of wood and a source of oil used for multiple purposes. The main and the most important oil component is 1,8-cineole (eucalyptol: 60%–85%). This review summarizes the literature reported to date involving the use of 1,8-cineole for the treatment of disorders. Additionally, we describe our efforts in the use of eucalyptol as a solvent for the synthesis of O,S,N-heterocycles. Solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, safety and health cannot be neglected. Green solvents such as bio-based systems hold considerable additional promise to reduce the environmental impact of organic chemistry. The first section outlines the process leading to our discovery of an unprecedented solvent and its validation in the first coupling reactions. This section continues with the description of its properties and characteristics and its reuse as reported in the various studies conducted. The second section highlights the use of eucalyptol in a series of coupling reactions (i.e., Suzuki–Miyaura, Sonogashira–Hagihara, Buchwald–Hartwig, Migita–Kosugi–Stille, Hiyama and cyanation) that form O,S,N-heterocycles. We describe the optimization process applied to reach the ideal conditions. We also show that eucalyptol can be a good alternative to build heterocycles that contain oxygen, sulfur and nitrogen. These studies allowed us to demonstrate the viability and potential that bio solvents can have in synthesis laboratories.

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“…This work began with a literature review to identify the best conditions for this kind of transformation. Once we had collected the main and most commonly used reaction conditions for the Buchwald-Hartwig coupling reaction, [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] we selected the conditions that mainly applied to the heterocycles frequently used by the team. The following conditions were identified as the starting point of this study ( Table 1).…”

Section: Introductionmentioning

confidence: 99%