Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group

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Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe₂ Group. / Mikshiev, Vladimir Y.; Antonov, Alexander S.; Pozharskii, Alexander F.

In: Organic Letters, Vol. 18, No. 12, 17.06.2016, p. 2872-2875.

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

BibTeX

@article{56b003eb204544c988c88703fb1f8177,

title = "Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group",

abstract = "It has been found that 2-bromo-1,8-bis(dimethylamino)naphthalene on sequential treatment with n-BuLi and 2 equiv of the same or different aryl(hetaryl) cyanide as a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe2/-N= analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe2 groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process is remarkable by surprisingly mild nucleophilic displacement of an unactivated aromatic NMe2 group.",

author = "Mikshiev, {Vladimir Y.} and Antonov, {Alexander S.} and Pozharskii, {Alexander F.}",

year = "2016",

month = jun,

day = "17",

doi = "10.1021/acs.orglett.6b01178",

language = "English",

volume = "18",

pages = "2872--2875",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

RIS

TY - JOUR

T1 - Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group

AU - Mikshiev, Vladimir Y.

AU - Antonov, Alexander S.

AU - Pozharskii, Alexander F.

PY - 2016/6/17

Y1 - 2016/6/17

N2 - It has been found that 2-bromo-1,8-bis(dimethylamino)naphthalene on sequential treatment with n-BuLi and 2 equiv of the same or different aryl(hetaryl) cyanide as a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe2/-N= analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe2 groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process is remarkable by surprisingly mild nucleophilic displacement of an unactivated aromatic NMe2 group.

AB - It has been found that 2-bromo-1,8-bis(dimethylamino)naphthalene on sequential treatment with n-BuLi and 2 equiv of the same or different aryl(hetaryl) cyanide as a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe2/-N= analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe2 groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process is remarkable by surprisingly mild nucleophilic displacement of an unactivated aromatic NMe2 group.

UR - http://www.scopus.com/inward/record.url?scp=84975481690&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b01178

DO - 10.1021/acs.orglett.6b01178

M3 - Article

AN - SCOPUS:84975481690

VL - 18

SP - 2872

EP - 2875

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -

ID: 41270767