Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Титов, А. А.; Samavati, Reza; Alexandrova, Elena V.; Борисова, Т. Н.; Thi, Tuyet Anh Dang; Nguyen, Van Tuyen; Lê, Tuấn Anh; Варламов, А. В.; Eycken, Erik V. Van der; Voskressensky, Leonid G.

doi:10.3390/molecules23113010

Cited by 3 publications

(1 citation statement)

References 21 publications

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“…One mechanism (Route A) is 1,3-migration of the N-allyl group (Route A), while the other involves tandem reactions (Route B). To investigate the direct 1,3-migration mechanism which is similar to 1,2-migration of Stevens rearrangement [19][20][21][22] we performed the reaction with substrates bearing N-propyl (saturated) or N-benzyl groups. This failed to provide the expected products, so rearrangement more likely occurred through tandem reactions even though we could not isolate any of the possible intermediates of tandem reactions.…”

Section: Proposed Mechanismmentioning

confidence: 99%

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

Choi

Mun

et al. 2019

Molecules

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The unexpected rearrangement of N-allyl-2-phenyl-4,5-dihydrooxazole-4-carboxamides in the presence of LiHMDS has been found. The key features are: (1) the net reaction consisted of 1,3-migration of the N-allyl group, (2) the rearrangement produced a congested aza-quaternary carbon center, (3) both cyclic and acyclic substrates underwent the unexpected rearrangement to afford products in moderate to high yields, and (4) the reaction seemed to be highly stereoselective. In addition, a plausible mechanism has been discussed.

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Section: Proposed Mechanismmentioning

confidence: 99%

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

Choi

Mun

et al. 2019

Molecules

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Synthetic Approaches Towards the Synthesis of C-1 Azole Substituted Tetrahydroisoquinolines

Singh

2021

COC

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: C-1 substituted tetrahydroisoquinolines have emerged as important scaffolds in pharmaceutical and medical research. Although various methods for α-substitution on tetrahydroisoquinolines have been discovered, the introduction of azole group at C-1 position remains a challenge. Recently, direct C-H activation methods and multicomponent reactions have been employed towards synthesis of azole containing tetrahydroisoquinolines. A summary of such synthetic strategies is presented here as these promising methods can help in developing more efficient synthetic routes. This minireview covers the available synthetic methods and their mechanistic pathways for the preparation of C-1 azole substituted tetrahydroisoquinolines.

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The chemistry of heterocycles in the 21st century

Charushin,

Verbitskiy,

Chupakhin

et al. 2024

RUSS CHEM REV

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The chemistry of heterocyclic compounds has traditionally been and remains a bright area of chemical science in Russia. This is due to the fact that many heterocycles find the widest application. These compounds are the key structural fragments of most drugs, plant protection agents. Many natural compounds are also derivatives of heterocycles. At present, more than half of the hundreds of millions of known chemical compounds are heterocycles. This collective review is devoted to the achievements of Russian chemists in this field over the last 15–20 years. The review presents the achievements of leading heterocyclists representing both RAS institutes and university science. It is worth noting the wide scope of the review, both in terms of the geography of author teams, covering the whole of our large country, and in terms of the diversity of research areas. Practically all major types of heterocycles are represented in the review. The special attention is focused on the practical applications of heterocycles in the design of new drugs and biologically active compounds, high-energy molecules, materials for organic electronics and photovoltaics, new ligands for coordination chemistry, and many other rapidly developing areas. These practical advances would not be possible without the development of new fundamental transformations in heterocyclic chemistry.<br> Bibliography — 2237 references.

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Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Cited by 3 publications

References 21 publications

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

Unexpected Rearrangement of N-Allyl-2-phenyl-4,5-Dihydrooxazole-4-Carboxamides to Construct Aza-Quaternary Carbon Centers

Synthetic Approaches Towards the Synthesis of C-1 Azole Substituted Tetrahydroisoquinolines

The chemistry of heterocycles in the 21st century

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