Tetrahedron Letters

An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride-promoted generation of α-carboxamidoalkylating electrophiles.

GR Moe, LM Sayre, PS Portoghese

Index: Moe, Gregory R.; Sayre, Lawrence M.; Portoghese, Philip S. Tetrahedron Letters, 1981 , vol. 22, # 6 p. 537 - 540

Full Text: HTML

Citation Number: 16

Abstract

Abstract Attempted N, N-dibenzoylation of aminomethanesulfonic acid results in C S bond cleavage, generating synthetically useful α-benzamidomethylating electrophiles. The importance of this observation in regard to the reported failures to prepare sulfonamide analogs of peptides is discussed.

Related Articles:

Green and efficient synthesis of sulfonamides catalyzed by nano-Ru/Fe3O4

[Shi, Feng; Tse, Man Kin; Zhou, Shaolin; Pohl, Marga-Martina; Radnik, Joerg; et al. Journal of the American Chemical Society, 2009 , vol. 131, p. 1775 - 1779]

Regioselective synthesis of N-substituted-4-substituted isothiazolidine-1, 1-dioxides

[Cleator, Ed; Sheen, Faye J.; Bio, Matthew M.; Jos Brands; Davies, Antony J.; Dolling, Ulf-H. Tetrahedron Letters, 2006 , vol. 47, # 25 p. 4245 - 4248]

Di-μ-hydroxy-bis (N, N, N′, N′-tetramethylenediamine)-copper (II) chloride [Cu (OH)· TMEDA] 2 Cl 2: an efficient, practical catalyst for benzylation and allylation of …

[Kumaraswamy; Pitchaiah; Ramakrishna; Sadaiah Tetrahedron Letters, 2006 , vol. 47, # 12 p. 2013 - 2015]

TiCl4-mediated direct N-alkylation of sulfonamides with inactive ethers

[Chen, Jiayan; Dang, Ling; Li, Qiang; Ye, Yong; Fu, Shaomin; Zeng, Wei Synlett, 2012 , # 4 p. 595 - 600]

Carbon radical addition to N-sulfonylimines mediated by triethylborane or zinc

[Ueda, Masafumi; Miyabe, Hideto; Miyata, Okiko; Naito, Takeaki Tetrahedron, 2009 , vol. 65, # 7 p. 1321 - 1326]

More Articles...