Acetylenchemie 6. Mitt.: Propinylierung von <i>N</i>‐Methylbarbitursäuren nach dem PTC‐ und phosphoroxychlorid‐verfahren ‐ nachweis zweier mechanismen bei der chromenbildung von pyrano[3,2‐<i>c</i>]chinolin‐alkaloiden

Reisch, J.; Bathe, A.

doi:10.1002/jhet.5570240536

Cited by 11 publications

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“…In 1987, Reisch and Bathe provided a procedure for the synthesis of dihydrofuro[2,3‐ d ]pyrimidines 60 in 13% yield via the reaction of 4a with 3‐chloro‐3‐methylbut‐1‐in in the presence of NaOH/H 2 O/Bu 4 NBr in toluene for 3 days (Scheme 24) [41].…”

Section: Synthesis Of Dihydrofuro[23‐d]pyrimidinesmentioning

confidence: 99%

Review on synthetic approaches towards barbituric acids‐based furo[2,3‐d]pyrimidines

Olyaei,

Sadeghpour

2023

Journal of Heterocyclic Chem

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Pyrimidine annulated five‐membered heterocyclic scaffolds containing oxygen as furopyrimidine, particularly furo[2,3‐d]pyrimidine derivatives are an important class of heterocyclic compounds in pharmaceutical discovery research. Furo[2,3‐d]pyrimidines are generally synthesized either from a pyrimidine derivative by constructing a furan ring on the parent pyrimidine ring or from a suitably functionalized furan ring by generating the pyrimidine ring on the parent furan ring. Moreover, there is a wide range of multicomponent reactions that include barbituric acids as starting material for the synthesis of these compounds. Also, the reaction of barbituric acids with alkenes, alkynes, aldehydes, ketones, ninhydrin, and chloroacetylchloride, and Cloke–Wilson rearrangement of spirocyclopropyl barbiturates afforded furo[2,3‐d]pyrimidine derivatives. This review is an attempt to compile the literature of various synthetic procedures toward barbituric acids‐based furo[2,3‐d]pyrimidine and spirofuro[2,3‐d]pyrimidines.

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Section: Synthesis Of Dihydrofuro[23‐d]pyrimidinesmentioning

confidence: 99%

Review on synthetic approaches towards barbituric acids‐based furo[2,3‐d]pyrimidines

Olyaei,

Sadeghpour

2023

Journal of Heterocyclic Chem

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“…pyrimidine derivative 98 49. A u g 2 of compound 96 with 1,1-diphenylethene (99) in warm acetic acid and manganese(Π) acetate as catalyst afforded 5-hydro-1,3-dimethyl-5,6-diphenylfuro[2,3-d]pyrimidin-2,4-(1H,3H)-dione (100)prepared by Perkin condensation of aromatic aldehydes with compound 96, react with phenylisocyanide to yield 5-aryl-6-phenylamino-1,3-dimethylfuro[2,3-d]pyrimidin-2,4-(1H,3H)-diones (101).On the other hand, treatment of 1,3-diaryl-2-thiobarbituric acid (102) with benzoin (103) in the presence of a catalytic amount of p-toluenesulphonic acid gave the corresponding furo[2,3-d] pyrimidines 104., Ph, C 6 H 4 Me-o, C 6 H 4 Me-m, C 6 H 4 Me-p, C 6 H 4 Cl-p, C 6 H 4 OMe-p A u g 2 5 , 2 0 1 3 Also, acylation of compound 102 with chloroacetyl chloride (105) in the presence of triethylamine gave 5-chloroacetyl derivative 106, which on cyclization with ethanolic sodium acetate gave the 5-oxo derivatives 107, C 6 H 4 Me-m, C 6 H 4 Me-p,C 6 H 4 Cl-p, C 6 H 4 Br-p,C 6 H 4 OMe-oOn the other hand, treatment of 5-chloroacetyl-1,3-dimethylbarbituric acid (108a) or 5-chloroacetyl-1,3-diethyl-2thiobarbituric acid (108b) with triethylamine resulted in cyclization and gave 1,3-dimethylfuro[2,3-d]pyrimidine-2,4,5(1H,3H,6H)-trione (109a) and 1,3-dimethylfuro[2,3-d]pyrimidine-2(1H)-thione-4,5(3H,6H)-dione (109b) respectively.O, R = Me b, X = S, R = Et 108 109a, X= O, R = Me b, X = S, R = Et Similarly, the reaction can be started with 5,5-disubstituted barbituric acid derivatives in which one of the substituents possesses some reactive group.…”

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confidence: 99%