The Preparation of Some 6-Substituted-2-thiouracils<sup>1</sup>

Jackman, Mary; Bergman, Arieh; Archer, Sydney

doi:10.1021/ja01182a019

Cited by 25 publications

(6 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We next investigate the scope and generality of the three established methods by using a variety of structurally diverse primary amides. 29 The results indicated that the three methods displayed wide substrate scope and good functional group compatibility, affording the desired nitriles in good-to-excellent yields (Table 2). The reactions proceeded efficiently with aliphatic, aromatic, and heteroaromatic carboxamides bearing electron-withdrawing or electron-donating groups.…”

Section: Resultsmentioning

confidence: 96%

See 1 more Smart Citation

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃

Talbi

Touil

2018

ACS Omega

View full text Add to dashboard Cite

Three efficient and high-yielding procedures have been developed for the conversion of primary amides into nitriles, mediated by hitherto unexplored P(NMe 2 ) 3 , PCl 3 , or P(OPh) 3 . The reactions were conducted under operationally simple and mild conditions and displayed broad substrate scope and good functional group tolerance.

show abstract

Section: Resultsmentioning

confidence: 96%

“…We next investigate the scope and generality of the three established methods by using a variety of structurally diverse primary amides . The results indicated that the three methods displayed wide substrate scope and good functional group compatibility, affording the desired nitriles in good-to-excellent yields (Table ).…”

Section: Resultsmentioning

confidence: 99%

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃

Talbi

Touil

2018

ACS Omega

View full text Add to dashboard Cite

show abstract

“…Spectroscopic data of compound 5 are in accordance with the literature. [37] Compounds 2, [38] 7, [39] 8, [9] 13, [40] 14, [41] and 17 [42] were synthesized according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Ravelli

Albini

Fagnoni

2010

Chemistry A European J

View full text Add to dashboard Cite

A mild and general method for the synthesis of potentially bioactive 2-substituted-1,3-benzodioxoles is presented. This is based on the photocatalyzed activation of methylene hydrogen atoms in the presence of tetrabutylammonium decatungstate (TBADT). The method gave yields ranging from 46-77 % with no interference by benzene ring substituents, such as OR, COOMe, Me, or CHO. The OH group interfered, but protection regenerated the reactivity. 5-Chloro-1,3-benzodioxole was converted into a safrole derivative through a one-pot process involving two consecutive irradiations, at 366 nm for the photocatalyzed alkylation at position 2 and at 310 nm for the alkylation at position 5.

show abstract

“…The resulting mixture was extracted with toluene (3 x 100 ml). The toluene extracts were concentrated, and the resulting solid was recrystallized (benzenehexane) to afford 25.4 g (28%) of 10, mp 54-55" (lit [33] Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic Acid Ethyl Ester (lg).…”

Section: Cyanocyclopentylideneacetic Acid Ethyl Ester (10)mentioning

confidence: 99%

Mechanistic observations in the gewald syntheses of 2‐aminothiophenes

Peet

Sunder

Barbuch

et al. 1986

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The Gewald syntheses were employed to prepare a series of 2-amino-3-carboethoxythiophenes, and the syntheses of two of these, namely, the 3,4-trimethylene (If) and 3,4tetramethylene (Ig) derivatives, were examined in detail. In two preparations of If, octahydro-6a~4morpholinyl~2-thioxocyclopent~~]pyrro~e~3-carboxylic acid (7) was a co-product. The structure of 7 was ascertained from its 300 MHz 'H nmr and 'X nmr spectra, and by its conversion to 1,4,5,6-tetrahydro-2-mercaptocyclopent~~]pyrrole-3-carboxylic acid ethyl ester (8). Isolation of 7 and other observations led to postulated mechanisms for three of the Gewald thiophene syntheses.

show abstract

The Preparation of Some 6-Substituted-2-thiouracils¹

Cited by 25 publications

References 2 publications

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃

Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Mechanistic observations in the gewald syntheses of 2‐aminothiophenes

Contact Info

Product

Resources

About

The Preparation of Some 6-Substituted-2-thiouracils1

Cited by 25 publications

References 2 publications

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe2)3, PCl3, or P(OPh)3

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe2)3, PCl3, or P(OPh)3

Smooth Photocatalytic Preparation of 2‐Substituted 1,3‐Benzodioxoles

Mechanistic observations in the gewald syntheses of 2‐aminothiophenes

Contact Info

Product

Resources

About

The Preparation of Some 6-Substituted-2-thiouracils¹

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃

Efficient New Protocols for Converting Primary Amides into Nitriles Initiated by P(NMe₂)₃, PCl₃, or P(OPh)₃