One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

Prajapati, Dipak; Baruah, Partha Pratim; Gogoi, Baikuntha J.; Sandhu, Jagir S.

doi:10.1186/1860-5397-2-5

Cited by 9 publications

(2 citation statements)

References 29 publications

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“…To overcome the limitation of harsh conditions led us to apply microwave-assisted chemistry; in fact, our efforts have not only led to improved yields but also opened new ways to the syntheses of otherwise hardly accessible polycyclic ring systems. [8,9] Further recent examples of type 2 tert-amino effect, including syntheses of pyrazolinoquinolizines and 1,4-oxazinopyrazolines, [10] 1,2-fused 5H-chromeno [4,3-b]pyridin-5-ones and 6H-benzo[h] [1,6] naphthyridin-5-ones, [11] naphthalenes, [12] a-carbolines, [13] and spirocyclic 1,2,3,4-tetrahydroquinolines, [14] also demonstrate the versatility of such reactions.…”

Section: Introductionmentioning

confidence: 99%

Study on the scope of tert‐amino effect: new extensions of type 2 reactions to bridged biaryls

Bottino

Schlich

Galavotti

et al. 2012

J of Physical Organic Chem

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Thermal isomerization of aminomethyl‐ or oxygen‐bridged biphenyl systems possessing dicyanovinyl and sec‐amino groups in ortho‐ and ortho′‐positions was investigated. Both systems underwent cyclization via tert‐amino effect. Thus, 2‐(2‐{[2‐(sec‐amino)benzyl]‐N‐methylamino}benzylidene)malononitriles gave tetrahydroquinolines, whereas a 2‐[2‐(sec‐amino)phenoxy]benzylidenemalononitrile isomerized to dibenzoxazonine derivative. The ring closure reaction was studied by differential scanning calorimetry measurements. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Study on the scope of tert‐amino effect: new extensions of type 2 reactions to bridged biaryls

Bottino

Schlich

Galavotti

et al. 2012

J of Physical Organic Chem

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“…In 2006, Prajapati et al [ 50 ] reacted 1,3‐dimethyl‐6‐hydrazinouracil 109 with an α‐ketoalkyne (3‐hexyn‐2‐one) in refluxing ethanol, the formed intermediate 110 could undergo a 5‐ exo‐trig cyclization in preference to 7‐ exo‐trig . The corresponding 2,4‐dioxo‐pyrazolo[3,4‐ d ]pyrimidines 111 were obtained instead of the expected seven‐membered pyrimido[1,2]diazepines 112 (Scheme 39).…”

Section: Synthetic Routes Of Pyrazolo[34‐d]pyrimidinesmentioning

confidence: 99%

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

Kassab

2022

Archiv der Pharmazie

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The pyrazolo[3,4‐d]pyrimidine core has received a lot of interest from the medicinal chemistry community as a promising framework for drug design and discovery. It is an isostere of the adenine ring of adenosine triphosphate, which allows it to mimic kinase active site hinge region binding contacts. This scaffold has a wide pharmacological and biological value, one of which is as an anticancer agent. Many successful anticancer medicines have been designed and synthesized using pyrazolo[3,4‐d]pyrimidine as a key pharmacophore. The main synthetic routes of pyrazolo[3,4‐d]pyrimidines as well as their recent developments as promising anticancer agents acting as endothelial growth factor receptors and vascular endothelial growth factor receptor inhibitors, published in the time frame from 1999 to 2022, are summarized in this review to set the direction for the design and synthesis of novel pyrazolo[3,4‐d]pyrimidine derivatives for clinical deployment in cancer treatment.

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The Use of 2-Chloro-4H-4-oxo-pyrido[1,2-a]pyrimidine as a Building Block in the Synthesis of Some New Heterocyclic Compounds

Badawy

Awad

Abdel‐Galil

2013

J. Heterocyclic Chem.

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in Wiley Online Library (wileyonlinelibrary.com). New approaches for the synthesis of some heterocyclic compounds, such as the pyridopyrimidodiazepine derivative 3, pyrazolopyrido[1,2-a]pyrimidine derivative 4, tetrazolo[1.5-a][1,8]naphthyridine derivative 9, pyrazolylpyrido[1,2-a]pyrimidine derivatives 10a,b,12, pyrrolopyrido[1,2-a]pyrimidine derivatives 14a-d, and16a,b, starting from 2-chloro-4H-4-oxo-pyrido[1,2-a]pyrimidine (1), are described.

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One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

Abstract: Novel 1H-pyrimido [4,5-c][1,2]diazepines 3 & 4 and pyrazolo [3,4-d]pyrimidines 6 were regioselectively synthesised by the reaction of 1,3-dimethyl-6-hydrazinouracils 1 with various α,β-unsaturated compounds 2 and α-ketoalkynes 8 in excellent yields.

Cited by 9 publications

References 29 publications

Study on the scope of tert‐amino effect: new extensions of type 2 reactions to bridged biaryls

Study on the scope of tert‐amino effect: new extensions of type 2 reactions to bridged biaryls

Pyrazolo[3,4‐d]pyrimidine scaffold: A review on synthetic approaches and EGFR and VEGFR inhibitory activities

The Use of 2-Chloro-4H-4-oxo-pyrido[1,2-a]pyrimidine as a Building Block in the Synthesis of Some New Heterocyclic Compounds

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