A new synthesis of pyrrolo[3,2-d]pyrimidines ("9-deazapurines") via 3-amino-2-carboalkoxypyrroles

Lim, Mu-Ill; Klein, Robert S.; Fox, Jack J.

doi:10.1021/jo01336a017

Cited by 38 publications

(31 citation statements)

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“…Thus, compound 7a was stirred at room temperature in methanolic ammonia to produce 4-aminopyrrolopyrimidine 9 and not the isomeric form 10 (Scheme 2). Attempts to obtain 9 from 8a according to literature methods 17 failed. The identity of pyrrolopyrimidine 9…”

Section: Methodsmentioning

confidence: 99%

3-Aminopyrroles and their application in the synthesis of pyrrolo[3,2-d]pyrimidine (9-deazapurine) derivatives

Salaheldin

Oliveira‐Campos²,

Rodrigues³

2008

Arkivoc

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Section: Methodsmentioning

confidence: 99%

3-Aminopyrroles and their application in the synthesis of pyrrolo[3,2-d]pyrimidine (9-deazapurine) derivatives

Salaheldin

Oliveira‐Campos²,

Rodrigues³

2008

Arkivoc

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“…Les composes 11 sont obtenus dans les memes conditions que 2, par reaction de l'enolate de sodium du 2-formyl-2-phi.nylacCtonitrile (10) [9] sur les chlorohydrates d'aniino-esters. Les ktudes analytiques (RMN, HPLC) prouvent que l'isomere ( Z ) des cyanoenamino-esters 11 est le seul produit formk; ces rksultats confirment et gentralisent ceux de Lim et collaborateurs [7].…”

Section: I)unclassified

“…~ Les solvants utilises en synthkse sont distilles avant emploi: le THF et l'Et20 sur Na/benzophknone, le CH2C12 sur CaH,, le CHCI, sur CaCI, et I'Et,N ,15 (m,MeCH2CH(h4e)); 1,33 ( t , 'J = 7, MeCH20); 1,2 (m,CH,de Ccp,MeCH,CH(Me)); 2,8 (m,2 CH,de Ccp);4,04,5 (m,MeCH,O,); 5,05 (d,,J = 10,NH). 5,2 (m,NH); 7,lO (d,,J = 13,C=CH);7,7 (m,5 H arom.). 3J = 7,MeCH20); 3,lO (d,,J = 6,5,PhCH,); 3,94,3 (m. H-C(2)); 4,20 (4,' J = 7,MeCH20); 5,84,2 (m = 13, C=CH); 7,15-7,7 (m, 5 H arom.).…”

Section: Ncunclassified

“…J = 7,MeCH,O); 3,50 (d, ' J = 7, H-C(2)); 7,20 (s,C=CH);7,80 (m,5 H arom.). (d. 3J = 6,5,Me,CH,CH); 126 (t. 3J = 6,5,MeCH,O); 1,9 (m. Me,CH,CH); 3,35 (s,MeN); 3,84,2 (m. H-C(2)); 4,20 ((I,3J = 7,MeCH,O); 7,20 (s,C=CH);7,[3][4][5][6][7]6 (m,5 H arom. CDC1,): 1,20 (t,' J = 7,MeCH2O); 3,lO (d, 3J = 6,5,CPhCH,); 3,23 (s, MeN); 3,74,1 (m, H-C(2)); 4,20 (q, ' J = 7, MeCH20); 7,05 (s, C=CH); 7,15-7,6 (m, 10 H arom. = …”

Section: Ncmentioning

confidence: 99%

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Les β‐cétonitriles groupes protecteurs de la fonction amine. Préparation d'amino‐alcools

Abarbri

Guignard

Lamant

1995

Helvetica Chimica Acta

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/l-Ketonitrile-Derived Protecting Groups of the Amino Function. Synthesis of Amino AlcoholsThe amino group of natural L-amino acid esters is protected by condensation with 2-oxocyclopentanenitrile (1) or 2-formyl-2-pheny~dtetonitrik (10). Only the ester group of the formed cyanoenamino esters 2 and 11 reacts with nucleophilic reagent!; such as organometallics (RMgX, RLi), borohydrides, or metal amides, whereas the cyanoenamino group is unchanged (Schemes I and 2). Cyanoenamino alcohols obtained by reduction of cyanoenamino esters 2 are hydrolyzed under acidic conditions to amino alcohols with retention of the configuration of the starting amino acid. This sequence of reactions allows to prepare derivatives of L-tyrosinol from (-)-L-tyrosine (see, e.g., Scheme 4 ) . Cyanoenamino esters 11 are readily methylated at the N-atom to give N-methylated cyanoenamino esters (Scheme 3 ) . This property is exploited on the way of a multistep procedure to obtain N-methylated amino alcohols homologous to natural (-)-(1 R,2S)-ephedrine.Introduction. -Nous avons deji d6crit [l] [2] la preparation des amino-alcools 4 a partir d'esters d'amino-acides naturels, dont la fonction amino est masquke sous forme cyanohamino dtrivt du 2-oxocyclopentanenitrile (1; schirna 1 ). La fonction ester des cyanotnamino-esters 2 (Z = OR3) peut subir diverses attaques nucltophiles qui ne modifient pas la configuration d'origine. Si le reactif nucleophile 'Nu' mis en jeu est un organomktallique (KMgX ou RLi), on obtient des cyanoenamino-alcools optiquement actifs 3 (R' = R2 = alkyle ou aryle), le groupe cyanotnamino restant inchangt [l]. Si 'Nu' est un amidure, l'esttx est transformi: en amide disubstitut 5 (Z = N R R ) avec conservation de l'activitk optique; il est ensuite possible d'acceder, par action du phenyllithium (PhLi), aux cetones ,aromatiques correspondantes 6 (Z = Ph), puis par action du NaBH, dans I'EtOH, aux alcools secondaires 3 (R' = H, R2 = Ph) [2]. L'tlimination du groupe protecteur 2-cyanocyclopent-1 -enyle (Ccp) effectuke par hydrolyse acide conduit finalement aux amino-alcools 4 et au reactif 1 (schPrna I ) . Ces rtactions s'effectuent sans racemisation [3].

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“…These include the synthesis of 2-(alkoxycarbonyl)-3-ureidopyrroles derived from pyrrole-2,3-dicarboxylic acid via Curtius rearrangement of the 3-acyl-azide intermediate [33], and condensation of a-amino-a-cyano-acetamides with ethyl acetoacetate followed by cyclization to ethyl 3-amino-2-carboxamido-5-methylpyrrole-4-carboxylate [34]. Several alkyl 3-aminopyrrole-2-carboxylates have been obtained by the base-catalyzed cyclization of N-(2-cyanoethenyl)glycine esters [35]. These 3-aminopyrrole-2-carboxylates have served as intermediates in the synthesis of pyrrolo[3,2-d]pyrimidines (9-deazapurines), 9-deazaguanozines, and other pyrrolo[3,2-d]pyrimidine C-nucleosides [36].…”

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confidence: 99%

Transformations of Ethyl 3-{[1-(Alkoxycarbonyl)-2-(dimethylamino)ethenyl]amino}-2-cyanoprop-2-enoates: Synthesis of Dialkyl 3-Aminopyrrole-2,4-dicarboxylates

Selič

Stanovnik

1998

HCA

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A new synthesis of pyrrolo[3,2-d]pyrimidines ("9-deazapurines") via 3-amino-2-carboalkoxypyrroles

Cited by 38 publications

References 0 publications

3-Aminopyrroles and their application in the synthesis of pyrrolo[3,2-d]pyrimidine (9-deazapurine) derivatives

3-Aminopyrroles and their application in the synthesis of pyrrolo[3,2-d]pyrimidine (9-deazapurine) derivatives

Les β‐cétonitriles groupes protecteurs de la fonction amine. Préparation d'amino‐alcools

Transformations of Ethyl 3-{[1-(Alkoxycarbonyl)-2-(dimethylamino)ethenyl]amino}-2-cyanoprop-2-enoates: Synthesis of Dialkyl 3-Aminopyrrole-2,4-dicarboxylates

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