Rapid, Scalable Assembly of Stereochemically Rich, Mono- and Bicyclic Acyl Sultams

Asad, Naeem; Samarakoon, Thiwanka Bandara; Zang, Qin; Loh, Joanna K.; Javed, Salim; Hanson, Paul R.

doi:10.1021/ol403070w

Cited by 19 publications

(7 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further, the target scaffold is closely related to to acyl sulfams, the unnatural compounds that have been reported to encompass a variety of activities and recently, their seven-memebred analogues were described. 9 In the past, the synthesis of 2,3-dihydrobenzo[f ][1,2,5]thiadiazepin-4(5H)-one 1,1-dioxides (with R 1 limited to H or CH 3 ) was described with the application of traditional solutionphase chemistry. [5][6][7]10 Methylesters of glycine or alanine were used as the starting material.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Although compounds based on the benzo[ f ][1,2,5]thiadiazepine 1,1-dioxide scaffold have been rarely studied, their antiarrhythmic, anti-HIV, , and anticancer activity (Figure ) make these molecules attractive for medicinal chemistry. Further, the target scaffold is closely related to to acyl sulfams, the unnatural compounds that have been reported to encompass a variety of activities and recently, their seven-memebred analogues were described …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions

2016

View full text Add to dashboard Cite

Synthesis of 2,3-dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-dioxides from polymer-supported α-amino acids is described herein. Different α-amino acids immobilized on Wang resin were sulfonylated with various 2-nitrobenzenesulfonyl chlorides. The resulting 2-nitrobenzenesulfonamides were alkylated with alcohols according to the Fukuyama-Mitsunobu procedure. After reduction of the nitro group and cleavage from the polymer support, the final intermediates were reacted with thionyl chloride, and target compounds of good crude purity and acceptable overall yields were obtained. The chiral HPLC studies revealed the impact of the cyclization step on the resulting stereochemistry. The developed strategy allows for simple production of desired compounds with the application of parallel/combinatorial solid-phase synthesis using commercially available building blocks.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions

2016

View full text Add to dashboard Cite

show abstract

“…We provide a short summary of this methodology to introduce the reader to several of these highyielding routes in one place. Similar synthetic paths were reported previously by us and the Hanson group [36][37][38][39][40][41][42][43][44][45]. In this work we combine all our synthetic methods for sevenand eight-membered ring -N,N-, -N,O-, and -N,S-sultams to give readers a more complete picture of the use of vinyl sulfonamides as starting materials to generate sultams.…”

Section: Introductionmentioning

confidence: 71%

A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions

et al. 2015

View full text Add to dashboard Cite

A series of seven- and eight-membered ring -N,O-, -N,N-, and -N,S-sultams were effectively synthesized via tandem reactions involving oxa-, aza-, and thia-Michael addition to vinyl sulfonamides. These reactions are summarized here since they enrich current synthetic methodologies for sultams and provide a good example of sultam diversity-oriented synthesis. All reactions proceeded under relatively mild and environmentally friendly conditions, and all these reactions are quite suitable for the rapid preparation of sultam compound libraries, which are valuable for biological activity explorations.

show abstract

“…In 2014, Hanson and co‐workers developed another one‐pot, sequential protocol involving complementary ambiphile pairing (CAP) of vinyl sulfonamides 53.1 with a variety of unprotected amino acids 53.2 through aza‐Michael addition and subsequent intramolecular amidation for the preparation of diverse, C(sp 3 )‐rich mono‐ and bicyclic acyl sultams 53.3 in good yields (Scheme ) …”

Section: Metal‐free Synthesis Of Sultamsmentioning

confidence: 99%

Sultams: Recent Syntheses and Applications

Debnath¹,

Mondal²

2018

Eur J Org Chem

View full text Add to dashboard Cite

Sultams are very important scaffolds both in medicinal chemistry and in synthetic organic chemistry. Very important methodologies for the asymmetric and non‐asymmetric synthesis of sultams, including asymmetric synthesis with memory of chirality (MOC), have recently been developed. Nowadays sultams are tremendously widely applied both in the medicinal field and in the synthetic field for the synthesis of different natural and non‐natural heterocycles. This review covers the recent development (2011–June 2017) of powerful methodologies for the synthesis of sultams and their applications in various fields during this period. A critical view of the mechanisms of the developed methodologies together with the scope and limitations of these methods add an extra dimension to the text.

show abstract

Rapid, Scalable Assembly of Stereochemically Rich, Mono- and Bicyclic Acyl Sultams

Cited by 19 publications

References 38 publications

Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions

Solid-Phase Synthesis of 2,3-Dihydrobenzo[f][1,2,5]thiadiazepin-4(5H)-one 1,1-Dioxides with Three Diversity Positions

A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions

Sultams: Recent Syntheses and Applications

Contact Info

Product

Resources

About