The Experts below are selected from a list of 528 Experts worldwide ranked by ideXlab platform
Paul R. Hanson - One of the best experts on this subject based on the ideXlab platform.
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An RCM Strategy to Stereodiverse δ-Sultam Scaffolds
2015Co-Authors: María Jiménez-hopkins, Paul R. HansonAbstract:An asymmetric approach for the synthesis of substituted δ-Sultams with multiple synthetic handles is described. This study demonstrates the facile construction of a stereochemically diverse array of substituted δ-Sultams, more specifically substituted 3,4,5,6-dihydro 1,2-thiazine 1,1-dioxides. A pivotal Mitsunobu alkylation/RCM sequence is used to assemble key allyl Sultam building blocks possessing a C3 stereogenic handle. All subsequent reactions are achieved with high levels of diastereoselectivity to afford enantiopure δ-Sultams in good yields. Compounds containing the sulfonamide moiety have gained wide popularity due to their extensive chemical and biological profiles, making them promising candidates in drug discovery.1 Sultams (cyclic sulfonamides), although not found in nature,2 have also shown potent biological activity, including several with medicinal value. A brief survey of the literature reveals that there are more than 60 Sultams with impressive biological activity. The more prominent include the antiepileptic agent sulthiame (1) (Figure 1),3 brinzolamide (2)4 for the treatment of glaucoma, the COX-2 inhibitors ampiroxicam (3)5 and S-2474 (4),6 novel benzodithiazine dioxides with both antiviral and anticancer activities (5),7a selective inhibitor
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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
Synthesis, 2012Co-Authors: Farman Ullah, Paul R. Hanson, Qin Zang, Salim Javed, Patrick Porubsky, Benjamin Neuenswander, Gerald H. Lushington, Michael G. OrganAbstract:A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulated, tricyclic Sultam library, utilizing a Heck–aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vinylsulfonamides with batch microwave heating followed by a one-pot, sequential intramolecular aza-Michael cyclization/Boc-deprotection using MACOS. Subsequent cyclization with either 1,1′-carbonyldiimidazole or chloromethyl pivalate using MACOS provided an array of tricyclic Sultams. This efficient three-step protocol requires only a few hours to produce the target Sultams starting from simple starting materials. Using this strategy, a 38-member library of isoindoline-annulated Sultams was generated in good to excellent overall yields (53–87%).
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synthesis of a unique isoindoline tetrahydroisoquinoline based tricyclic Sultam library utilizing a heck aza michael strategy
ACS Combinatorial Science, 2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Fatima Z. Basha, Michael G. Organ, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/ THIQ and secondary sulfonamides precursors, were constructed using this strategy.
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Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Michael G. Organ, Fatima Z. Basha, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1′-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy
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Metathesis cascade strategies (ROM-RCM-CM): a DOS approach to skeletally diverse Sultams
Tetrahedron, 2009Co-Authors: Kyu Ok Jeon, Dinesh Kumar Rayabarapu, Alan Rolfe, Kelly A. Volp, Iman Omar, Paul R. HansonAbstract:The development of a ring-opening metathesis/ring-closing metathesis/cross metathesis (ROM-RCM-CM) cascade strategy to the synthesis of a diverse collection of bi- and tricyclic Sultams is reported. In this study, functionalized Sultam scaffolds derived from intramolecular Diels-Alder (IMDA) reactions undergo metathesis cascades to yield a collection tricyclic Sultams. Additional appendage based diversity was achieved by utilizing a variety of CM partners.
Michael G. Organ - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
Synthesis, 2012Co-Authors: Farman Ullah, Paul R. Hanson, Qin Zang, Salim Javed, Patrick Porubsky, Benjamin Neuenswander, Gerald H. Lushington, Michael G. OrganAbstract:A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulated, tricyclic Sultam library, utilizing a Heck–aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vinylsulfonamides with batch microwave heating followed by a one-pot, sequential intramolecular aza-Michael cyclization/Boc-deprotection using MACOS. Subsequent cyclization with either 1,1′-carbonyldiimidazole or chloromethyl pivalate using MACOS provided an array of tricyclic Sultams. This efficient three-step protocol requires only a few hours to produce the target Sultams starting from simple starting materials. Using this strategy, a 38-member library of isoindoline-annulated Sultams was generated in good to excellent overall yields (53–87%).
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synthesis of a unique isoindoline tetrahydroisoquinoline based tricyclic Sultam library utilizing a heck aza michael strategy
ACS Combinatorial Science, 2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Fatima Z. Basha, Michael G. Organ, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/ THIQ and secondary sulfonamides precursors, were constructed using this strategy.
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Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Michael G. Organ, Fatima Z. Basha, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1′-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy
Qin Zang - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
Synthesis, 2012Co-Authors: Farman Ullah, Paul R. Hanson, Qin Zang, Salim Javed, Patrick Porubsky, Benjamin Neuenswander, Gerald H. Lushington, Michael G. OrganAbstract:A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulated, tricyclic Sultam library, utilizing a Heck–aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vinylsulfonamides with batch microwave heating followed by a one-pot, sequential intramolecular aza-Michael cyclization/Boc-deprotection using MACOS. Subsequent cyclization with either 1,1′-carbonyldiimidazole or chloromethyl pivalate using MACOS provided an array of tricyclic Sultams. This efficient three-step protocol requires only a few hours to produce the target Sultams starting from simple starting materials. Using this strategy, a 38-member library of isoindoline-annulated Sultams was generated in good to excellent overall yields (53–87%).
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synthesis of a unique isoindoline tetrahydroisoquinoline based tricyclic Sultam library utilizing a heck aza michael strategy
ACS Combinatorial Science, 2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Fatima Z. Basha, Michael G. Organ, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/ THIQ and secondary sulfonamides precursors, were constructed using this strategy.
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Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Michael G. Organ, Fatima Z. Basha, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1′-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy
Farman Ullah - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of an Isoindoline-Annulated, Tricyclic Sultam Library via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)
Synthesis, 2012Co-Authors: Farman Ullah, Paul R. Hanson, Qin Zang, Salim Javed, Patrick Porubsky, Benjamin Neuenswander, Gerald H. Lushington, Michael G. OrganAbstract:A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of an isoindoline-annulated, tricyclic Sultam library, utilizing a Heck–aza-Michael (HaM) strategy, is reported. This sequence involves a Heck reaction on vinylsulfonamides with batch microwave heating followed by a one-pot, sequential intramolecular aza-Michael cyclization/Boc-deprotection using MACOS. Subsequent cyclization with either 1,1′-carbonyldiimidazole or chloromethyl pivalate using MACOS provided an array of tricyclic Sultams. This efficient three-step protocol requires only a few hours to produce the target Sultams starting from simple starting materials. Using this strategy, a 38-member library of isoindoline-annulated Sultams was generated in good to excellent overall yields (53–87%).
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synthesis of a unique isoindoline tetrahydroisoquinoline based tricyclic Sultam library utilizing a heck aza michael strategy
ACS Combinatorial Science, 2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Fatima Z. Basha, Michael G. Organ, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/ THIQ and secondary sulfonamides precursors, were constructed using this strategy.
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Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
2012Co-Authors: Qin Zang, Salim Javed, Patrick Porubsky, Farman Ullah, Benjamin Neuenswander, Gerald H. Lushington, Michael G. Organ, Fatima Z. Basha, Paul R. HansonAbstract:The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic Sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cyclization with either paraformaldehyde condensation or 1,1′-carbonyldiimidazole coupling generates a variety of tricyclic Sultams. Overall, a 160-member library of these Sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy
Reza Kia - One of the best experts on this subject based on the ideXlab platform.
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one pot three component synthesis of novel δ Sultam scaffolds via n sulfonylation intramolecular michael sequences
ChemInform, 2012Co-Authors: Mehdi Ghandi, Seyed Hadi Nazari, Abolfazl Hasani Bozcheloei, Masoud Sadeghazadeh, Reza KiaAbstract:One-pot three-component reaction of 1,3-dicarbonyl compounds, styrenesulfonyl chlorides and amines is supposed to proceed via N-sulfonylation—intramolecular Michael addition sequence to yield novel δ-Sultam derivatives.
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one pot three component synthesis of novel δ Sultam scaffolds via n sulfonylation intramolecular michael sequences
Tetrahedron Letters, 2011Co-Authors: Mehdi Ghandi, Seyed Hadi Nazari, Abolfazl Hasani Bozcheloei, Masoud Sadeghzadeh, Reza KiaAbstract:Abstract The synthesis of novel δ-Sultam scaffolds utilizing one-pot, three-component reactions of 1,3-dicarbonyl compounds, primary aliphatic amines and substituted styrenesulfonyl chlorides is reported. A variety of six-membered Sultams are obtained in moderate to good yields presumably via N-sulfonylation—intramolecular Michael addition sequences.
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One-pot, three-component synthesis of novel δ-Sultam scaffolds via N-sulfonylation—intramolecular Michael sequences.
Tetrahedron Letters, 2011Co-Authors: Mehdi Ghandi, Seyed Hadi Nazari, Abolfazl Hasani Bozcheloei, Masoud Sadeghzadeh, Reza KiaAbstract:Abstract The synthesis of novel δ-Sultam scaffolds utilizing one-pot, three-component reactions of 1,3-dicarbonyl compounds, primary aliphatic amines and substituted styrenesulfonyl chlorides is reported. A variety of six-membered Sultams are obtained in moderate to good yields presumably via N-sulfonylation—intramolecular Michael addition sequences.
