2022
DOI: 10.1039/d1nj05332a
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Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

Abstract: A facile synthesis of [5,5]-annulated N-fused heterocycles – pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via oxidative [3+2]-annulation between nitroalkenes and azolium ylides in the presence of copper (II) was developed. The reaction proceeds...

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Cited by 5 publications
(5 citation statements)
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“…Reaction conditions: (i) Ag 2 CO 3 , THF, reflux; [17] (ii) Et 3 N, CHCl 3 ; [18] (iii) 2,6-lutidine, Cu(OAc) 2 , DCE; [19] (iv) 2,6-lutidine, Cu(OAc) 2 , DMSO. [20]…”
Section: Resultsmentioning
confidence: 99%
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“…Reaction conditions: (i) Ag 2 CO 3 , THF, reflux; [17] (ii) Et 3 N, CHCl 3 ; [18] (iii) 2,6-lutidine, Cu(OAc) 2 , DCE; [19] (iv) 2,6-lutidine, Cu(OAc) 2 , DMSO. [20]…”
Section: Resultsmentioning
confidence: 99%
“…Initially, we attempted to prepare compound 3 , which does not contain substituents in a pyridine ring, based on the oxidative 1,3‐dipolar cycloaddition reaction between pyridinium ylide generated under basic conditions in situ from the corresponding salt 1 and α‐nitrostilbene 2 (Scheme 1). We exploited several previously described synthetic procedures using Ag 2 CO 3 in THF, [17] Et 3 N in CHCl 3 , [18] 2,6‐lutidine–Cu(OAc) 2 system in DCE [19] and in DMSO, [20] and DABCO‐MnO 2 system in toluene . [21] However, in all cases a mixture of a minor amount of the desired product of [3+2]‐cycloaddition 3 and a major amount of compound 3′ has been obtained.…”
Section: Resultsmentioning
confidence: 99%
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“…To date, there is one reported example of a pyrazolium ylide reacting via formal 1,3-dipolar cycloaddition (Scheme 1B). [13] Building on our group's recent work functionalizing the 3position of pyrazoles by combining the corresponding N-oxides with arynes (Scheme 1C), [14] we envisioned that we could promote formal [3 + 2] cycloadditions of pyrazolium ylides with electrophiles to form nitrogen-containing heterocyclic scaffolds. In this work, we report a mild, transition metal free method to form indolizine and pyrimidine derivatives from pyrazolium ylide precursors.…”
Section: Introductionmentioning
confidence: 99%
“…Elegant work from the Levin lab employs chlorodiazirines to promote ring expansion of pyrazoles and afford pyrimidine products through N ‐ N cleavage and subsequent carbon atom insertion [8] (Scheme 1A). To date, there is one reported example of a pyrazolium ylide reacting via formal 1,3‐dipolar cycloaddition (Scheme 1B) [13] . Building on our group's recent work functionalizing the 3‐ position of pyrazoles by combining the corresponding N ‐oxides with arynes (Scheme 1C), [14] we envisioned that we could promote formal [3+2] cycloadditions of pyrazolium ylides with electrophiles to form nitrogen‐containing heterocyclic scaffolds.…”
Section: Introductionmentioning
confidence: 99%