Design, two-directional synthesis, DFT study of new pyrimido[5,4-d]pyrimidine-2,8-dione derivatives

Sheykhi-Estalkhjani, Ammar; Mahmoodi, Nosrat O.; Yahyazadeh, Asieh; Nadamani, Meysam Pasandideh; Nahzomi, Hossein Taherpour

doi:10.1016/j.tet.2018.12.057

Cited by 7 publications

(4 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The formation of the bis-1,3,4,7-tetrahydropyrimido[5,4- d ]pyrimidine-2,8-diones 182 was illustrated in a reported mechanism by the nucleophilic addition of the copper complex formed with phenyl urea 2 to the bis-aldehydes (181) (in a molar ratio of 2 : 1) and subsequent cyclocondensation of the formed intermediates, a H-shift and an oxidative cyclization step. 91 …”

Section: Synthetic Methodsmentioning

confidence: 99%

Bicyclic 6 + 6 systems: the chemistry of pyrimido[4,5-d]pyrimidines and pyrimido[5,4-d]pyrimidines

et al. 2019

View full text Add to dashboard Cite

show abstract

Section: Synthetic Methodsmentioning

confidence: 99%

Bicyclic 6 + 6 systems: the chemistry of pyrimido[4,5-d]pyrimidines and pyrimido[5,4-d]pyrimidines

et al. 2019

View full text Add to dashboard Cite

show abstract

“…[5,14] Functionalised pyrimidine derivatives were transformed into pyrimidopyrimidine by reaction with nucleophiles/eletrophiles [6,15] Acyclic diaminomaleonitrile derivatives were also used as starting reagents in reaction with aldehydes. [16,17] Purine derivatives were likewise used to generate the pyrimidopyrimidine nucleus by nucleophilic addition of amines. [6,18,19] In recent years our research group efficiently generated an isomeric skeleton of pyrimido [5,4d]pyrimidine, the 7,8-dihydropyrimidopyrimidine 2, from 9-aryl-6-cyanopurines 1 according to Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…Many pyrimidopyrimidine derivatives were obtained from its parent chloropyrimido[5,4‐ d ]pyrimidine by substitution of the chlorine atom by a convenient amine [5,14] . Functionalised pyrimidine derivatives were transformed into pyrimidopyrimidine by reaction with nucleophiles/eletrophiles [6,15] Acyclic diaminomaleonitrile derivatives were also used as starting reagents in reaction with aldehydes [16,17] . Purine derivatives were likewise used to generate the pyrimidopyrimidine nucleus by nucleophilic addition of amines [6,18,19] .…”

Section: Introductionmentioning

confidence: 99%

A Tandem Reaction in the Synthesis of New 4,8‐Disubstituted‐pyrimido[5,4‐d]pyrimidine Derivatives

Rocha,

Lopes,

Teixeira

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

Pyrimido[5,4‐d]pyrimidines are biologically important compounds with diverse activity depending on the substituent groups around the heterocycle. The 3,4‐dihydropyrimido[5,4‐d]pyrimidines are efficiently converted to the aromatic derivatives by Dimroth rearrangement promoted by reaction with piperidine, in a very slow process. Subsequently, the aromatic derivatives are converted to new 4,8‐disubstituted‐pyrimido[5,4‐d]pyrimidine derivatives by reaction with aldehydes in an acidic medium. The 4,8‐disubstituted‐pyrimido[5,4‐d]pyrimidines are also obtained much more efficiently by a tandem reaction between the 3,4‐dihydropyrimido[5,4‐d]pyrimidines, piperidine and a variety of aldehydes. The cascade reaction approach has a broad application since phenyl, haloaryl, alkoxy‐aryl, hydroxy‐aryl, and heteroaryl aldehydes are compatible with the reaction conditions. The reactions were studied by 1H NMR. These studies support the reaction mechanisms proposals. The tandem approach involves the formation of ionic reactive intermediates that allows explain this approach's efficiency.

show abstract

“…26 The chemical reactivity study is incomplete without the combination of experimental results with the theoretical study. Ammar et al 27 studied the synthesis of new pyrimido [5,4-d]pyrimidine-2,8-dione via the reaction of premade bis-aldehydes and 1-(2-amino-1,2-dicyanovinyl)-3-phenylurea with triethylamine as the base and Cu (II) as the catalyst. They found that using B3LYP/6-31+G(d)/LANL2DZ method, the formation of sixmembered pyrimidine ring is the most favorable pathway of this process yielding to the major product.…”

Section: Introductionmentioning

confidence: 99%

Decoding the reaction mechanism of the cyclocondensation of ethyl acetate2‐oxo‐2‐(4‐oxo‐4H‐pyrido [1.2‐a] pyrimidin‐3‐yl) polyazaheterocycle and ethylenediamine using bond evolution theory

et al. 2022

View full text Add to dashboard Cite

We investigated the flow of electron density along the cyclocondensation reaction between ethyl acetate 2-oxo-2-(4-oxo-4H-pyrido[1.2-a]pyrimidin-3-yl) polyazaheterocycle (1) and ethylenediamine (2) at the ωB97XD/6-311++G(d,p) computational method within of bond evolution theory (BET). The exploration of potential energy surface shows that this reaction has three channels (1-3) with the formation of product 3 via channel-2 (the most favorable one) as the main product and this is in good agreement with experimental observations. The BET analysis allows identifying unambiguously the main chemical events happening along channel-2. The mechanism along first step (TS2-a) is described by a series of four structural stability domains (SSDs), while five SSDs for the last two steps (TS2-b and TS2-c). The first and third steps can be summarized as follows, the formation of N1-C6 bond (SSD-II), then, the restoration of the nitrogen N1 lone pair (SSD-III), and finally, the formation of the last O1-H1 bond (SSD-IV). For the second step, the formation of hydroxide ion is noted, as a result of the disappearance of V(C6,O7) basin and the transformation of C6-N1 single bond into double one

show abstract

Design, two-directional synthesis, DFT study of new pyrimido[5,4-d]pyrimidine-2,8-dione derivatives

Cited by 7 publications

References 32 publications

Bicyclic 6 + 6 systems: the chemistry of pyrimido[4,5-d]pyrimidines and pyrimido[5,4-d]pyrimidines

Bicyclic 6 + 6 systems: the chemistry of pyrimido[4,5-d]pyrimidines and pyrimido[5,4-d]pyrimidines

A Tandem Reaction in the Synthesis of New 4,8‐Disubstituted‐pyrimido[5,4‐d]pyrimidine Derivatives

Decoding the reaction mechanism of the cyclocondensation of ethyl acetate2‐oxo‐2‐(4‐oxo‐4H‐pyrido [1.2‐a] pyrimidin‐3‐yl) polyazaheterocycle and ethylenediamine using bond evolution theory

Contact Info

Product

Resources

About