TY - JOUR

T1 - Synthesis and cyclization of 1-arylalk-1-ene-3,5-diynylamines

AU - Sorokoumov, V. N.

AU - Morozkina, S. N.

AU - Balova, I. A.

PY - 2006/5/1

Y1 - 2006/5/1

N2 - An investigation of the reaction of 1-lithio-1,3-diynes, generated in situ, with nitriles has been carried out. In the case of aromatic nitriles 1-arylalk-1-ene-3,5-diynylamines are formed, which undergo dimerization and cyclization on isolation, giving 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6- diarylpyridines. The effect of the nature of the substituent in the benzonitrile molecule on the selectivity of the reaction and the yield of the products has been determined. A scheme is proposed for the conversions and the structures of the intermediates have been established.

AB - An investigation of the reaction of 1-lithio-1,3-diynes, generated in situ, with nitriles has been carried out. In the case of aromatic nitriles 1-arylalk-1-ene-3,5-diynylamines are formed, which undergo dimerization and cyclization on isolation, giving 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6- diarylpyridines. The effect of the nature of the substituent in the benzonitrile molecule on the selectivity of the reaction and the yield of the products has been determined. A scheme is proposed for the conversions and the structures of the intermediates have been established.

KW - 1-arylalk-1-en-3,5-diynylamines

KW - 1-lithio-1,3-diynes

KW - 3-(alka-1,3-diynyl)-4-(alk-2-ynyl)-2,6-diarylpyridines

KW - Diacetylenes

KW - Lithium 2-aminoethylamide

KW - Nitriles

KW - Prototropic isomerization

UR - http://www.scopus.com/inward/record.url?scp=33748162732&partnerID=8YFLogxK

U2 - 10.1007/s10593-006-0136-9

DO - 10.1007/s10593-006-0136-9

M3 - Article

AN - SCOPUS:33748162732

VL - 42

SP - 615

EP - 624

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 5

ER -