Investigation of Masked N‐Acyl‐N‐isocyanates: Support for Oxadiazolones as Blocked N‐Isocyanate Precursors
In contrast to carbon‐substituted isocyanates that are common building blocks, N‐substituted isocyanates remain underdeveloped and reports on their N‐acyl derivatives (i. e. amido‐isocyanates) are exceedingly rare. Herein, amido‐isocyanates were investigated in the context of syntheses of aza‐tripep...
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Published in | Chemistry : a European journal Vol. 27; no. 56; pp. 14051 - 14056 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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07.10.2021
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Abstract | In contrast to carbon‐substituted isocyanates that are common building blocks, N‐substituted isocyanates remain underdeveloped and reports on their N‐acyl derivatives (i. e. amido‐isocyanates) are exceedingly rare. Herein, amido‐isocyanates were investigated in the context of syntheses of aza‐tripeptide and hydantoins subunits starting from simple bench‐stable precursors. A key finding is that the amido‐isocyanate formed in situ cyclized to yield an oxadiazolone, and that under suitable reaction conditions this heterocycle is a traceless blocked (masked) N‐isocyanate. Using organic bases as catalysts and upon heating, oxadiazolone formation is observed, and various nucleophiles to provide the desired aza‐dipeptides or hydantoins in moderate to high yields. Further support for an amido‐isocyanate intermediate was obtained using carboxylic acids as nucleophiles, affording N‐acylhydrazide products.
Masked synthesis: N‐isocyanates are reactive intermediates and their N‐acyl derivatives, amido‐isocyanates, are rare. Herein, their synthesis and reactivity are studied, supporting that under suitable conditions the amido‐isocyanate is in equilibrium with the parent oxadiazolone. Reactions with amino‐amides as nucleophiles form nitrogen‐rich products, either aza‐tripeptides or their parent hydantoins. Support for an isocyanate intermediate was also obtained using carboxylate ions as nucleophiles, affording N‐acylhydrazides. |
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AbstractList | Abstract
In contrast to carbon‐substituted isocyanates that are common building blocks,
N
‐substituted isocyanates remain underdeveloped and reports on their
N
‐acyl derivatives (i. e. amido‐isocyanates) are exceedingly rare. Herein, amido‐isocyanates were investigated in the context of syntheses of aza‐tripeptide and hydantoins subunits starting from simple bench‐stable precursors. A key finding is that the amido‐isocyanate formed in situ cyclized to yield an oxadiazolone, and that under suitable reaction conditions this heterocycle is a traceless blocked (masked)
N
‐isocyanate. Using organic bases as catalysts and upon heating, oxadiazolone formation is observed, and various nucleophiles to provide the desired aza‐dipeptides or hydantoins in moderate to high yields. Further support for an amido‐isocyanate intermediate was obtained using carboxylic acids as nucleophiles, affording
N
‐acylhydrazide products. In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl derivatives (i. e. amido-isocyanates) are exceedingly rare. Herein, amido-isocyanates were investigated in the context of syntheses of aza-tripeptide and hydantoins subunits starting from simple bench-stable precursors. A key finding is that the amido-isocyanate formed in situ cyclized to yield an oxadiazolone, and that under suitable reaction conditions this heterocycle is a traceless blocked (masked) N-isocyanate. Using organic bases as catalysts and upon heating, oxadiazolone formation is observed, and various nucleophiles to provide the desired aza-dipeptides or hydantoins in moderate to high yields. Further support for an amido-isocyanate intermediate was obtained using carboxylic acids as nucleophiles, affording N-acylhydrazide products. In contrast to carbon‐substituted isocyanates that are common building blocks, N‐substituted isocyanates remain underdeveloped and reports on their N‐acyl derivatives (i. e. amido‐isocyanates) are exceedingly rare. Herein, amido‐isocyanates were investigated in the context of syntheses of aza‐tripeptide and hydantoins subunits starting from simple bench‐stable precursors. A key finding is that the amido‐isocyanate formed in situ cyclized to yield an oxadiazolone, and that under suitable reaction conditions this heterocycle is a traceless blocked (masked) N‐isocyanate. Using organic bases as catalysts and upon heating, oxadiazolone formation is observed, and various nucleophiles to provide the desired aza‐dipeptides or hydantoins in moderate to high yields. Further support for an amido‐isocyanate intermediate was obtained using carboxylic acids as nucleophiles, affording N‐acylhydrazide products. Masked synthesis: N‐isocyanates are reactive intermediates and their N‐acyl derivatives, amido‐isocyanates, are rare. Herein, their synthesis and reactivity are studied, supporting that under suitable conditions the amido‐isocyanate is in equilibrium with the parent oxadiazolone. Reactions with amino‐amides as nucleophiles form nitrogen‐rich products, either aza‐tripeptides or their parent hydantoins. Support for an isocyanate intermediate was also obtained using carboxylate ions as nucleophiles, affording N‐acylhydrazides. |
Author | O'Keefe, Geneviève F. Lutes, Owen C. Jeanneret, Alexandria D. M. Blanger, Claire Ivanovich, Ryan A. Gagné‐Monfette, William Vincent‐Rocan, Jean‐François Beauchemin, André M. |
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Keywords | SOLID-PHASE SYNTHESIS ONE-POT SYNTHESIS AMINO INHIBITION aza-peptides isocyanates nitrogen heterocycles CONCERTED CYCLOADDITIONS oxadiazolones hydrazides AZA-PEPTIDE AMIDE BOND FORMATION PEPTIDE-SYNTHESIS DERIVATIVES AZAPEPTIDES |
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Snippet | In contrast to carbon‐substituted isocyanates that are common building blocks, N‐substituted isocyanates remain underdeveloped and reports on their N‐acyl... In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl... Abstract In contrast to carbon‐substituted isocyanates that are common building blocks, N ‐substituted isocyanates remain underdeveloped and reports on their N... |
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SubjectTerms | aza-peptides Carboxylic acids Catalysts Chemistry Chemistry, Multidisciplinary Hydantoin hydrazides Isocyanates nitrogen heterocycles Nucleophiles oxadiazolones Physical Sciences Precursors Science & Technology Substitutes |
Title | Investigation of Masked N‐Acyl‐N‐isocyanates: Support for Oxadiazolones as Blocked N‐Isocyanate Precursors |
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