New type of transannular reactions in azirine-fused medium-size heterocycles: Selective transformations of azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into oxa(thia)zine and oxa(thia)zole derivatives

Shinkevich, Ekaterina Yu.; Новиков, Михаил С.; Khlebnikov, Alexander F.; Kostikov, R. R.; Kopf, J.; Magull, Jörg

doi:10.1134/s1070428007070214

Cited by 12 publications

(2 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Benzoxazoheterocycles are the main structural element of some biologically active molecules, 1 2 3 4 5 6 7 8 9 10 and are also found in extracts obtained from natural sources (Figure 1 ). 11…”

mentioning

confidence: 99%

“…Benzoxazoheterocycles are the main structural element of some biologically active molecules, [1][2][3][4][5][6][7][8][9][10] and are also found in extracts obtained from natural sources (Figure 1). 11 The various approaches to the synthesis of the compounds with such backbones make it possible to construct the heterocycles with the required regiolocalization of the nitrogen, oxygen atoms, and functional groups.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Гатауллин¹

2023

Synthesis

View full text Add to dashboard Cite

A significant influence of the nature of the acyl substituent at the nitrogen atom on the direction of the reaction in the interaction of N-acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines with bromine was found. In the case of the N-benzoyl derivative, along with benzoxazocinone, which is formed through the stages of pseudoallyl halogenation and subsequent lactonization due to the replacement of the bromine atom by the oxygen atom of the carboxyl group, a mixture of axially chiral isomers of spiro-fused 2′-bromocyclohexane-benzoxazepin-3-ones was also obtained. The aR*,R*,R*-isomer of benzoxazepinone, which initially is four times predominant in the reaction mixture, upon dissolution in deuterochloroform, slowly transforms into aS*-conformer until a ratio of 2:1 is established. In the case of the N-acetyl analogue of this glycine, the only heterocycle is the product of 7-exo-halogenlactonization, the benzoxazepinone spiro-fused with 2′-bromocyclohexane and an undetermined configuration of the axial chirality.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Гатауллин¹

2023

Synthesis

View full text Add to dashboard Cite

show abstract

Ring‐Opening/Ring‐Closing Protocols from Nitrothiophenes: Six‐Membered versus Unusual Eight‐Membered Sulfur Heterocycles through Michael‐Type Addition on Nitrobutadienes

Bianchi

Giorgi

Maccagno

et al. 2010

Chemistry A European J

View full text Add to dashboard Cite

When Ar is a low-aromaticity homo- or heterosystem, the sulfonyl-stabilized anion of nitrobutadienes 4 (which derive from the initial ring opening of 3-nitrothiophene) undergoes a rather surprising addition onto the aromatic ring itself, thereby leading to the construction of an unusual eight-membered sulfur heterocycle condensed with the original Ar ring. The competitiveness of such a pathway with respect to the formation of the thiopyran ring (i.e., addition onto the nitrovinyl moiety) is favored at low temperatures, thus revealing its nature as a kinetically controlled process.

show abstract

ChemInform Abstract: New Type of Transannular Reactions in Azirine‐Fused Medium‐Size Heterocycles: Selective Transformations of Azirino[2,1‐e][1,6]benzoxazocines and ‐benzothiazocines into Oxa(thia)zine and Oxa(thia)zole Derivatives.

et al. 2008

View full text Add to dashboard Cite

Azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into Oxa(thia)zine and Oxa(thia)zole Derivatives. -Ring opening of the aziridine ring of heterocyclic systems, e.g. (III) and (XII), leads to benzoxazines and benzothiazines, respectively. Depending on the conditions, benzoxazoles [cf. (VI)-(VIII)] are available. -(SHINKEVICH, E. Y.; NOVIKOV, M. S.; KHLEBNIKOV*, A. F.; KOSTIKOV, R. R.; KOPF, J.; MAGULL, J.; Russ.

show abstract

New type of transannular reactions in azirine-fused medium-size heterocycles: Selective transformations of azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into oxa(thia)zine and oxa(thia)zole derivatives

Cited by 12 publications

References 29 publications

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Ring‐Opening/Ring‐Closing Protocols from Nitrothiophenes: Six‐Membered versus Unusual Eight‐Membered Sulfur Heterocycles through Michael‐Type Addition on Nitrobutadienes

ChemInform Abstract: New Type of Transannular Reactions in Azirine‐Fused Medium‐Size Heterocycles: Selective Transformations of Azirino[2,1‐e][1,6]benzoxazocines and ‐benzothiazocines into Oxa(thia)zine and Oxa(thia)zole Derivatives.

Contact Info

Product

Resources

About