Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes

Standard

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes. / Kadina, A. P.; Novikov, M. S.; Khlebnikov, A. F.; Magull, J.

In: Chemistry of Heterocyclic Compounds, Vol. 44, No. 5, 01.05.2008, p. 576-584.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{774acc5e860f466d9871a63f1e14562c,

title = "Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes",

abstract = "The reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbene to give (1RS,5SR,6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7- trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes has been studied. Quantum-chemical calculations using the DFT B3LYP/6-31G(d) method have confirmed that the mechanism of the reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation.",

keywords = "Aziridines, Carbenes, Cascade reactions, Domino reactions, Imidazoles, Iminium ylides, Pyrimidines",

author = "Kadina, {A. P.} and Novikov, {M. S.} and Khlebnikov, {A. F.} and J. Magull",

year = "2008",

month = may,

day = "1",

doi = "10.1007/s10593-008-0077-6",

language = "English",

volume = "44",

pages = "576--584",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Nature",

number = "5",

}

RIS

TY - JOUR

T1 - Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6- diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0] hept-2-enes

AU - Kadina, A. P.

AU - Novikov, M. S.

AU - Khlebnikov, A. F.

AU - Magull, J.

PY - 2008/5/1

Y1 - 2008/5/1

N2 - The reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbene to give (1RS,5SR,6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7- trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes has been studied. Quantum-chemical calculations using the DFT B3LYP/6-31G(d) method have confirmed that the mechanism of the reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation.

AB - The reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbene to give (1RS,5SR,6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7- trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes has been studied. Quantum-chemical calculations using the DFT B3LYP/6-31G(d) method have confirmed that the mechanism of the reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation.

KW - Aziridines

KW - Carbenes

KW - Cascade reactions

KW - Domino reactions

KW - Imidazoles

KW - Iminium ylides

KW - Pyrimidines

UR - http://www.scopus.com/inward/record.url?scp=53249118907&partnerID=8YFLogxK

U2 - 10.1007/s10593-008-0077-6

DO - 10.1007/s10593-008-0077-6

M3 - Article

AN - SCOPUS:53249118907

VL - 44

SP - 576

EP - 584

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 5

ER -

ID: 28187850