Isonitriles from the Baylis–Hillman adducts of acrylates: viable precursor to tetrazolo-fused diazepinones via post-Ugi cyclization

Nayak, Maloy; Batra, Sanjay

doi:10.1016/j.tetlet.2009.11.051

Cited by 35 publications

(14 citation statements)

References 20 publications

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“…In a variation, Nayak and Batra reported an Ugi/hydrolysis/coupling sequence starting from allyl isonitrile 266 that was synthesized from its corresponding primary allyl amine 265 , which in turn was derived from Baylis–Hillsman acrylates [ 203 ]. The tetrazole-based Ugi adducts 267 were obtained in high to excellent yields (60–86%), that via subsequent ester-hydrolysis and coupling with EDC and NMM resulted in the tetrazole-based BDPs 268 in overall yields of 47–67% ( Scheme 78 ).…”

Section: Reviewmentioning

confidence: 99%

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

Koopmanschap¹,

Ruijter²,

Orru³

2014

Beilstein J. Org. Chem.

233

117

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SummaryIn the recent past, the design and synthesis of peptide mimics (peptidomimetics) has received much attention. This because they have shown in many cases enhanced pharmacological properties over their natural peptide analogues. In particular, the incorporation of cyclic constructs into peptides is of high interest as they reduce the flexibility of the peptide enhancing often affinity for a certain receptor. Moreover, these cyclic mimics force the molecule into a well-defined secondary structure. Constraint structural and conformational features are often found in biological active peptides. For the synthesis of cyclic constrained peptidomimetics usually a sequence of multiple reactions has been applied, which makes it difficult to easily introduce structural diversity necessary for fine tuning the biological activity. A promising approach to tackle this problem is the use of multicomponent reactions (MCRs), because they can introduce both structural diversity and molecular complexity in only one step. Among the MCRs, the isocyanide-based multicomponent reactions (IMCRs) are most relevant for the synthesis of peptidomimetics because they provide peptide-like products. However, these IMCRs usually give linear products and in order to obtain cyclic constrained peptidomimetics, the acyclic products have to be cyclized via additional cyclization strategies. This is possible via incorporation of bifunctional substrates into the initial IMCR. Examples of such bifunctional groups are N-protected amino acids, convertible isocyanides or MCR-components that bear an additional alkene, alkyne or azide moiety and can be cyclized via either a deprotection–cyclization strategy, a ring-closing metathesis, a 1,3-dipolar cycloaddition or even via a sequence of multiple multicomponent reactions. The sequential IMCR-cyclization reactions can afford small cyclic peptide mimics (ranging from four- to seven-membered rings), medium-sized cyclic constructs or peptidic macrocycles (>12 membered rings). This review describes the developments since 2002 of IMCRs-cyclization strategies towards a wide variety of small cyclic mimics, medium sized cyclic constructs and macrocyclic peptidomimetics.

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Section: Reviewmentioning

confidence: 99%

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

Koopmanschap¹,

Ruijter²,

Orru³

2014

Beilstein J. Org. Chem.

233

117

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“…Another similar work by Nayak and Batra reports on MCRbased synthesis of tetrazolodiazepines starting from Baylis-Hillman adducts of acrylates (Scheme 34). 43 They have developed the stereocontrolled synthesis of substituted isonitriles from the Baylis-Hillman adducts of acrylates 78. Then, Ugi reaction of these isonitriles with TMSN 3 , aliphatic amines, and aldehydes or ketones affords substituted tetrazoles which have been demonstrated to be suitable substrates for producing tetrazolo-fused diazepinones 79.…”

Section: Synthesis Of Fused 15-disubstituted Tetrazoles Via Ugiazide ...mentioning

confidence: 99%

Synthesis of tetrazoles via isocyanide-based reactions

2015

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The aim of this review is providing an overview of the various representative literature procedures for the preparation of tetrazoles via isocyanide-based reactions. These reactions have been divided into four classes including two-component reactions (2CRs), Passerini-azide three-component reactions (PA-3CRs), Ugi-azide four-component reactions (UA-4CRs) and Ugi-azide three-component reactions (UA-3CRs).Scheme 1 Tetrazoles are bioisosteres of carboxylic acids and cisamides.Scheme 2 Cycloaddition reaction between isocyanides and HN 3 . Scheme 3 Synthesis of tetrazoles 3 under acid catalysis. Scheme 4 Synthesis of optically pure 1-STs. This journal is Scheme 8 Four-component synthesis of alkoxylated tetrazole 15 and a-alkoxyamides 16. Scheme 9 Synthesis of tetrazoles via intramolecular MCR of cyclic acetals. Scheme 10 The UA-4CR as a variation of the classical Ugi-reaction. 60942 | RSC Adv., 2015, 5, 60938-60955 This journal is Scheme 11 Synthesis of quinolin-4-amine-based tetrazoles 19. Scheme 12 Synthesis of 1,5-disubstituted aminomethyltetrazole derivatives 23. Scheme 13 A UA-4CR repetitive product. Scheme 14 Desosamine containing tetrazoles. This journal is Scheme 15 UA-4CR synthesis of tetrazolic analogues 28 of chalcones 27. Scheme 16 Synthesis of 4-aminoquinoline-tetrazole derivatives 30. 60944 | RSC Adv., 2015, 5, 60938-60955 This journal is Scheme 17 Synthesis of tetrazoles 32 in the presence of MgBr 2 $2Et 2 O. Scheme 18 The preparation of the tetrazole 33 by an UA-4CR. Scheme 19 Diastereoselective synthesis of a-hydrazine tetrazoles 32 via a UA-MCR. This journal isScheme 20 UA-4CRs for the synthesis of a-amino acid analogue tetrazoles 37.Scheme 21 Synthesis of tetrazolyl-isoindolinones 40 via UA-4CR/intramolecular amidation.Scheme 22 Synthesis of bis-3,4-dihydroquinoxalinone and bis-benzodiazepine tetrazoles. Scheme 23 Synthesis of 1,5-DT-hydantoins. 60946 | RSC Adv., 2015, 5, 60938-60955 This journal is Scheme 34 Synthesis of tetrazole-fused diazepinones through UA-MCRs. Scheme 35 Synthesis of tetrazolo-fused benzodiazepinones.Fig. 6 Examples of tetrazolo-fused benzodiazepinones 83 and benzodiazepines 86 and 87. This journal isScheme 41 Proposed mechanism for the formation of 1,5-DTs.Scheme 42 UA-3CR for the synthesis of tetrazolyl-pyridines, -quinoline and -isoquinoline.Scheme 43 Three-component process for the synthesis of 1,5-DT.Scheme 44 U-4C/3-CR for the synthesis of fused 1,5-DSTs.Scheme 45 Synthesis of the 5-halo-1-phenyltetrazoles.This journal is

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“…Recently, Nayak et al demonstrated the application of MW irradiation to the synthesis of novel tetrazoles via a Ugi four-component reaction (Scheme 17.10) [34]. The first key step involved four-component condensation and was conducted under MW heating to produce highly substituted 1,5-tetrazoles (82) in 60-86% yields.…”

Section: Cycloadditions Of Azidesmentioning

confidence: 99%