α-Aminoazoles/azines: key reaction partners for multicomponent reactions

Imtiaz, Shah; War, Jahangir Ahmad; Banoo, Syqa; Khan, Shabnam

doi:10.1039/d1ra00392e

Cited by 25 publications

(14 citation statements)

References 300 publications

(336 reference statements)

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“…In continuation of our research program in catalytic asymmetric reactions with dienecarbamates, [14] we decided to explore their reactivities in connection with 2‐benzothiazolimines. Indeed, these imines are versatile synthetic intermediates used for the syntheses of various heterocycles [15] and they have been embedded in direct catalytic asymmetric annulation strategies [2e–h] . With two latent nucleophiles ( N and N‘ ), we reasoned that they could be ideal linchpin for divergent pathways, [7] as a common intermediate generated upon addition of a dienecarbamate onto the imine, could eventually lead by ring closure either to a tetrahydropyridine motive or benzothiazolopyrimidine skeleton (Scheme 1c).…”

Section: Methodsmentioning

confidence: 99%

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines

Montinho-inacio

Iorga

et al. 2022

Adv Synth Catal

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An enantioselective chiral phosphoric acid catalyzed formal [4+2] cycloaddition between 2‐benzothiazolimines and N‐H‐1,3‐dienecarbamates is described. A divergence in reaction pathways was observed depending on the dienes employed. The reaction performed with 4‐substituted dienes produced benzothiazolopyrimidines as major product in yields ranging from 42 to 67%, as single diastereoisomer and with enantioselectivity between 93 and 99%. The same reaction performed with 3‐substituted dienes, however, gave highly enantioenriched 1,2,3,4‐tetrahydroquinolines as the major products albeit with moderate diastereoselectivity.

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Section: Methodsmentioning

confidence: 99%

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines

Montinho-inacio

Iorga

et al. 2022

Adv Synth Catal

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“…Indeed, it must be noted that handling low molecular isocyanides is relatively straightforward if one has a methanolic HCl solution on‐hand to re‐hydrate remnants of isocyanides on glassware, syringes or gloves. A wide range of reviews and book chapters in recent years on isocyanides articulate this peculiar transition new entrants to the field experience [88–96] …”

Section: Isocyanide Chemistrymentioning

confidence: 99%

“…A wide range of reviews and book chapters in recent years on isocyanides articulate this peculiar transition new entrants to the field experience. [88][89][90][91][92][93][94][95][96] In summary, we collectively hold the view that isocyanide chemistry is far from exhausted, and many new developments are expected in the field. At the end of the 20th century, the renaissance of isocyanide chemistry was driven by a lack of innovation and productivity in the pharmaceutical sector which led to a need for library compatible methodologies that could feasibly afford a broad spectrum of heterocyclic scaffolds, pseudopeptide structures and subsequent biologically active compounds.…”

Section: Isocyanide Chemistrymentioning

confidence: 99%

Six‐Component Reactions and Beyond: The Nuts and Bolts

Hooshmand

Yazdani²,

Hulme

2022

Eur J Org Chem

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The deployment of multicomponent reactions (MCRs), defined as containing three or more reactants, not only enjoys pot, atom, and step‐economy in the synthesis of novel complex molecules but also aligns with sustainable chemistry principles as a green symphony. Generally, more components lead to more complexity, and are taken to an extreme ‘‘higher‐order’’ MCRs, where six or even more components react in a one‐pot, have been developed, although they remain scarce compared to their 3, 4 and 5‐component relatives. On this topic, the rich footprint of isocyanides in MCRs has been fruitful in delivering higher order six to eight‐component reactions through mechanistically similar pathways. The present review encompasses a brief history of MCRs and their product utility, followed by a thorough discussion of the principles of reaction design that enabled the discovery of higher‐order MCRs, spanning 6 to 8‐components. Future challenges and opportunities will also be elaborated.

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“…Development in MCRs is notorious, especially over the last two decades [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. Today we have, via these multicomponent transformations, rapid and one-pot access to diverse and complex libraries of bioactive compounds and to synthetic molecules with technological potentials [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates

et al. 2022

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We discuss herein the problems associated with using melting points to characterize multicomponent reactions’ (MCRs) products and intermediates. Although surprising, it is not rare to find articles in which these MCRs final adducts (or their intermediates) are characterized solely by comparing melting points with those available from other reports. A brief survey among specialized articles highlights serious and obvious problems with this practice since, for instance, cases are found in which as many as 25 quite contrasting melting points have been attributed to the very same MCR adduct. Indeed, it seems logical to assume that the inherent non-confirmatory nature of melting points could be vastly misleading as a protocol for structural confirmation, but still many publications (also in the Q1 and Q2 quartiles) insist on using it. This procedure contradicts best practices in organic synthesis, and articles fraught with limitations and misleading conclusions have been published in the MCRs field. The drawbacks inherent to this practice are indeed serious and have misguided MCRs advances. We therefore suggest some precautions aimed at avoiding future confusions.

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α-Aminoazoles/azines: key reaction partners for multicomponent reactions

Abstract: Aromatic α-aminoazaheterocycles are the focus of significant investigations and exploration by researchers owing to their key role in diverse biological and physiological processes.

Cited by 25 publications

References 300 publications

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines

Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines

Six‐Component Reactions and Beyond: The Nuts and Bolts

In Melting Points We Trust: A Review on the Misguiding Characterization of Multicomponent Reactions Adducts and Intermediates

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