Synthesis and properties of 1-alkyl-2-methyl-3-sulfonylpyrroles and 1-alkyl-2-methyl-3-sulfonylpyrrole-5-carboxylic acid derivatives

Moranta, C.; Molins-Pujol, Antoni M.; Pujol, M. D.; Bonal, J.

doi:10.1039/a803239d

Cited by 7 publications

(4 citation statements)

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“…This intriguing preference for selective C3 substitution has yet to be rationalized in detail. When the pyrrole nucleus is already deactivated, sulfonation using acidic reagents is feasible, as illustrated by the transformation of the pyrrole 177 into the sulfonyl chloride 178 in 81% yield using chlorosulfonic acid [266]. Likewise, sulfonation of 1-(arylsulfonyl)pyrroles with chlorosulfonic acid in acetonitrile gives practical access to the corresponding pyrrole-3-sulfonyl chlorides in moderate yields [267].…”

Section: Nitrationmentioning

confidence: 98%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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Section: Nitrationmentioning

confidence: 98%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…[3+2]-annulation 6 followed by oxidation of the intermediate 3-pyrroline; c) cycloaddition involving sydnone or Nacyl pyrroles and alkynyl sulfones. 7,8 In our case, because of the wide range of arylsulfonyl chlorides commercially available, we chose to synthesise this derivative via functionalisation of the 3-lithio-TIPS pyrrole derivative, easily obtained from commercially available 3-bromo-TIPS pyrrole 4 (Scheme 2). 9…”

mentioning

confidence: 99%

Synthesis of Tetrasubstituted 2-Aryl-3-arylsulfonyl Pyrroles: Unexpected Regioselectivity in Directed ortho-Metallation Reactions

Bailey¹,

Demont²,

Garton³

et al. 2008

Synlett

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3-Arylsulfonyl pyrroles can be readily obtained from 3-Br-TIPS pyrrole via halogen-metal exchange and subsequent sulfonylation. The regioselectivity of the subsequent directed ortho-metallation (DOM) reaction in order to functionalise the C-2 position depends on the nature of the base (LTMP, n-or s-BuLi) and the Nsubstituent (SEM or Boc) used. The bulk of the N-substituent also strongly influences the yield of the subsequent Suzuki coupling with 2-iodo-3-arylsulfonyl pyrrole derivatives.

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“…We found that atmospheric oxygen oxidized this position, yielding the corresponding α -hydroxyl compound, when R 2 ≠ H. Other examples of oxidation of pyrroles with ceric ammonium nitrate (CAN) 6 and ceric triflate 7 have recently been reported. As part of our program to develop syntheses of functionally 3-substituted pyrroles we previously reported 8 the synthesis of a variety of compounds related to structure 3 with a sulfur-based electronwithdrawing group substituting position 3 on the pyrrole ring. In this paper, we report a preliminary study on the oxidation of the benzylic-type moiety in 3-nitropyrroles related to structure 1 and in 3-alkylaminosulfonylpyrroles 3 .…”

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confidence: 99%

“…Compounds 1a, 1b, 1d and 3aÐg were prepared following our recently published procedures. 5,8 Compound 1c was prepared from methyl 1-methyl-3-nitropyrrole-5-carboxylate, according to the method of Ballini et al 14…”

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confidence: 99%