Synthesis of pyrido[2,3-b]quinoxaline derivatives

Глушков, Р. Г.; Dronova, L. N.; Elina, A. S.; Musatova, I. S.; Porokhovaya, M. V.; Соловьева, Н. П.; Chistyakov, V. V.; Sheinker, Yu. N.

doi:10.1007/bf00758278

Cited by 3 publications

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“…In more recent work [26] it was possible to obtain lactim ethers with good yields (63)(64)(65) by reaction of the lactams 2 or 3 with the ester 10 at moderate temperature (40-45°C, 4 h; 25°C, 16 h) without a solvent.…”

Section: Reactions Of Lactams With Dialkyl Sulfates or Trialkyloxoniumentioning

confidence: 99%

“…More recently, however, the authors of [58] The mono-and bicyclic diketones 50 react with lactim ethers in boiling alcohol with the formation of compounds 51 [22]. The reactions of lactim ethers with the esters of β-oxo carboxylic acids 52 have been studied for many examples, and the keto esters 53 were synthesized [2,22,57,[59][60][61][62][63]. However, with R 2 = 2-FC 6 H 4 the reaction products were tricyclic compounds 54 as a result, clearly, of cyclization of the initially formed keto esters 53 [64].…”

Section: Reactions With Compounds Containing Activated Ch 2 Groupsmentioning

confidence: 99%

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Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Shvekhgeimer

2005

Chem Heterocycl Compd

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Section: Reactions Of Lactams With Dialkyl Sulfates or Trialkyloxoniumentioning

confidence: 99%

Section: Reactions With Compounds Containing Activated Ch 2 Groupsmentioning

confidence: 99%

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Shvekhgeimer

2005

Chem Heterocycl Compd

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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Synthesis of Pyrrolo[l,2-a]quinoxalines

Мамедов

2016

Quinoxalines

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Synthesis of pyrido[2,3-b]quinoxaline derivatives

Cited by 3 publications

References 3 publications

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Synthesis of Pyrrolo[l,2-a]quinoxalines

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