Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

Boschi, Donatella; Sorba, Giovanni; Bertinaria, Massimo; Fruttero, Roberta; Calvino, R.; Gasco, Alberto

doi:10.1039/b104845g

Cited by 29 publications

(10 citation statements)

References 12 publications

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“…It should be mentioned that the literature reports similar S → O [ 33 , 34 , 35 ] and S → N [ 36 , 37 , 38 , 39 ] type Smiles rearrangement. The possible mechanism of formation of compounds 4 is presented in Scheme 2 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Amino-3-oxo-2,7-naphthyridines via Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

Sirakanyan

Spinelli

Geronikaki

et al. 2022

IJMS

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In this paper we describe an efficient method for the synthesis of new heterocyclic systems: furo[2,3-c]-2,7-naphthyridines 6, as well as a new method for the preparation of 1,3-diamino-2,7-naphthyridines 11. For the first time, a Smiles rearrangement was carried out in the 2,7-naphthyridine series, thus gaining the opportunity to synthesize 1-amino-3-oxo-2,7-naphthyridines 4, which are the starting compounds for obtaining furo[2,3-c]-2,7-naphthyridines. The cyclization of alkoxyacetamides 9 proceeds via two different processes: the expected formation of furo[2,3-c]-2,7-naphthyridines 10 and the ‘unexpected’ formation of 1,3-diamino-2,7-naphthyridines 11 (via a Smiles type rearrangement).

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Amino-3-oxo-2,7-naphthyridines via Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

Sirakanyan

Spinelli

Geronikaki

et al. 2022

IJMS

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“…Interestingly, phenol 14a bearing a new C–O(H) bond was obtained by treating 1m with 2-mercaptoethan-1-ol in the presence of KHMDS as the base. Likely, a Smiles rearrangement of the initially formed aryl thioether to the aryl ether, followed by elimination of thiirane was involved in the transformation (Boschi et al., 2001). All these products can be used as key intermediates for further functional group transformation.…”

Section: Resultsmentioning

confidence: 99%

Non-transition Metal-Mediated Diverse Aryl–Heteroatom Bond Formation of Arylammonium Salts

et al. 2019

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Summary Aryl–heteroatom (C–X) bonds ubiquitously exist in organic, medicinal, and material chemistry, but a universal method to construct diverse C–X bonds is lacking. Here we report our discovery of a convenient and efficient approach to construct various C–X bonds using arylammonium salts as the substrate via an S N Ar process. This strategy features mild reaction condition, no request of transition metal catalyst, and easy formation of various C–X bonds (C–S, C–Si, C–Sn, C–Ge, C–Se, C–N). The method was successfully applied to a late-stage functionalization of an existing antibiotic drug, to a Clickable reaction of NBD-based ammonium salt as turn-on fluorescent probe to recognize L-cysteine and homocysteine, and to the synthesis of a DNA encoded library (DEL) bearing different C–X bonds.

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“…The A → C conversion was similar to the Smiles rearrangement accompanied by elimination of sulfur dioxide [20][21][22][23][24][25] SYNTHESIS OF METHYL 2-ARYL-5-CHLOROSULFONYL-1,3-OXAZOLE-4-CARBOXYLATES similar reaction pathway was observed in the case of interaction of 2-aryl-4-cyano-1,3-oxazole-5-sulfonyl chlorides with 5-amino-1H-pyrazoles and 5-amino-1H-1,2,4-triazoles to form tricyclic structures [14].…”

Section: Kornienko Et Al 1556mentioning

confidence: 88%

Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

et al. 2014

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Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

Cited by 29 publications

References 12 publications

Synthesis of 1-Amino-3-oxo-2,7-naphthyridines via Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

Synthesis of 1-Amino-3-oxo-2,7-naphthyridines via Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

Non-transition Metal-Mediated Diverse Aryl–Heteroatom Bond Formation of Arylammonium Salts

Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines

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