N–N Bond-Forming Cyclization for the One-Pot Synthesis of <i>N</i>-Aryl[3,4-<i>d</i>]pyrazolopyrimidines

Evans, Lindsey; Cheeseman, Matthew D.; Jones, Keith

doi:10.1021/ol301561a

Cited by 26 publications

(14 citation statements)

References 34 publications

(30 reference statements)

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“…Methods for constructing heterocycles that involve direct N–N bond formation are rare, yet desirable due to the drawbacks of working with hydrazine. 11–13 …”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

“…9,10 Synthetic methods for accessing these structural motifs are available, however developing new strategies for constructing X–X linkages is an active area of investigation in synthetic organic chemistry. 11–15 An underexplored but promising approach for accessing such scaffolds is the use of X–X bond forming enzymes in the context of biocatalysis and synthetic biology. Such applications could help to alleviate the relative lack of synthetic methods for X–X bond formation in comparison to C–C and C–X bond construction.…”

Section: Introductionmentioning

confidence: 99%

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Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

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Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X, where X = N, O, S, and P) are a small yet intriguing group of metabolites. The reactivity and diversity of these structural motifs has captured the interest of synthetic and biological chemists alike. Functional groups containing X–X bonds are found in all major classes of natural products and often impart significant biological activity. This review presents our current understanding of the biosynthetic logic and enzymatic chemistry involved in the construction of X–X bond containing functional groups within natural products. Elucidating and characterizing biosynthetic pathways that generate X–X bonds could both provide tools for biocatalysis and synthetic biology, as well as guide efforts to uncover new natural products containing these structural features.

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“…Methods for constructing heterocycles that involve direct N–N bond formation are rare, yet desirable due to the drawbacks of working with hydrazine. 11–13 …”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

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“…Under reductive conditions, [27] the major compound 27 (51 % isolated yield) afforded 8b in 88 % yield. In addition to being slightly more efficient, this second route to 8b also allowed recycling of the minor thioester 28, which, when treated with bromine, [28] led back to 9b. Scheme 6.…”

Section: Synthesis Of the Aldehydes 8a And 8bmentioning

confidence: 99%

Total Synthesis of (+)‐Brefeldin C, (+)‐nor‐Me Brefeldin A and (+)‐4‐epi‐nor‐Me Brefeldin A

et al. 2010

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International audienceA total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed, Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered lactone ring

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“…Another variant of N-N bond formation consists of the treatment of 4-aminopyrimidine-5-carbaldehydes with HOSA. The initially formed oxime-O-sulfonates undergo intramolecular electrophilic amination to give the expected N-aryl [3,4-d]pyrazolopyrimidines [56].…”

Section: Reactions With Heterocumulenesmentioning

confidence: 99%

Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

Sączewski

Korcz

2014

Heterocyclic Communications

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The heterocyclic hydroxylamine-O-sulfonates constitute a novel family of formal O-substituted hydroxyguanidines and hydroxyamidines that serve as functional precursors to a variety of fused heterocyclic ring systems incorporating N-N, N-O, N-S, or N-N + moiety. They are readily accessible from the reaction of 2-chloroazoles, 2-chloroazines, and 2-chlorodiazines with hydroxylamine-O-sulfonic acid. They have a rich chemistry exemplified by tandem reactions, such as nucleophilic addition-electrophilic amination, nucleophilic addition-electrophilic 5-endo-trig cyclization or fluorogenic Mannich-electrophilic amination reaction. The heterocyclic hydroxylamine-O-sulfonates have significant potential for use in synthesis of anticancer, antiviral, and antimicrobial agents. The newly discovered fluorogenic reaction and fluorescent dyes (Safirinium-P and Safirinium-Q) have found applications in fluorescent detection and labeling.

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N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines

Cited by 26 publications

References 34 publications

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

Total Synthesis of (+)‐Brefeldin C, (+)‐nor‐Me Brefeldin A and (+)‐4‐epi‐nor‐Me Brefeldin A

Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

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