Rh(III)-Catalyzed Imidoyl C–H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones

Confair, Danielle N.; Greenwood, Nathaniel S.; Mercado, Brandon Q.; Ellman, Jonathan A.

doi:10.1021/acs.orglett.0c03393

Cited by 8 publications

(2 citation statements)

References 21 publications

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“…A reaction of heterocyclic imines and (pivaloyloxy)carbamates provided bicyclic [1,3,5]triazinones using [Cp*Rh(MeCN) 3 ](SbF 6 ) 2 and pivalic acid (Scheme ). Switching the solvent from DCE to HFIP and using 3 Å MS facilitated a three-component approach relying on in situ generated imines.…”

Section: Condensationsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: Condensationsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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“…The APBTTs 1a-g were obtained according to reported procedures [21,25]. The compounds 2a-n were obtained according to the reported procedures [66][67][68][69][70][71][72][73][74][75][76][77][78][79][80]. Benzene, toluene, o-xylene, p-xylene, 1,4-dioxane, and THF for procedures with compounds 1 were distilled over Na before use.…”

Section: Methodsmentioning

confidence: 99%

Reaction of Pyrrolobenzothiazines with Schiff Bases and Carbodiimides: Approach to Angular 6/5/5/5-Tetracyclic Spiroheterocycles

Lystsova,

Novokshonova,

Khramtsov

et al. 2024

Molecules

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1H-Pyrrole-2,3-diones, fused at [e]-side with a heterocycle, are suitable platforms for the synthesis of various angular polycyclic alkaloid-like spiroheterocycles. Recently discovered sulfur-containing [e]-fused 1H-pyrrole-2,3-diones (aroylpyrrolobenzothiazinetriones) tend to exhibit unusual reactivity. Based on these peculiar representatives of [e]-fused 1H-pyrrole-2,3-diones, we have developed an approach to an unprecedented 6/5/5/5-tetracyclic alkaloid-like spiroheterocyclic system of benzo[d]pyrrolo[3′,4′:2,3]pyrrolo[2,1-b]thiazole via their reaction with Schiff bases and carbodiimides. The experimental results have been supplemented with DFT computational studies. The synthesized alkaloid-like 6/5/5/5-tetracyclic compounds have been tested for their biotechnological potential as growth stimulants in the green algae Chlorella vulgaris.

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Rhodium‐Catalyzed Heterocycle Synthesis by CH Functionalization

Cao

Kou

2022

Handbook of CH-Functionalization

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Rhodium complexes of +1, +2, and +3 oxidation states are adept at functionalizing CH bonds and do so via distinct mechanistic pathways. These modes of activation have been harnessed into cascade processes that lead to a wide variety of heterocycles, including isoquinolines, isoquinolones, pyridines, pyridones, indoles, lactones, and their fused polycyclic derivatives. As such, this article will focus on the chemistry that enables de novo synthesis of heterocycles rather than those that only functionalize existing heterocycles. This article is organized into three parts, starting with Part A, Rhodium(III) catalysis, which makes up the largest subfield of rhodium‐catalyzed heterocycle synthesis, and is further divided into the chemistry of alkynes, alkenes, carbenes, and nitrenes. Part B details rhodium(I) catalysis in the contexts of hydroalkenylation (e.g. alkynes), hydroarylation (e.g. alkynes), and hydroacylation (e.g. alkynes, alkenes, and ketones). The article closes with Part C, a brief discussion on the use of rhodium(II) catalysis in constructing heterocycles.

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Rh(III)-Catalyzed Imidoyl C–H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones

Cited by 8 publications

References 21 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

Reaction of Pyrrolobenzothiazines with Schiff Bases and Carbodiimides: Approach to Angular 6/5/5/5-Tetracyclic Spiroheterocycles

Rhodium‐Catalyzed Heterocycle Synthesis by CH Functionalization

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