The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings

Styliana I. Mirallai; Panayiotis A. Koutentis

doi:10.1021/acs.joc.5b01514

The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings

Styliana I. Mirallai
, Panayiotis A. Koutentis

School of Life and Health Sciences

University of Cyprus

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

Abstract

Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared in high yields via three new routes: (1) a Cu(OTf)₂ (0-5 mol %) catalyzed hypervalent iodine [PhI(OTf)₂] mediated oxidative coupling of 4-anilinoquinazoline-2-carbonitriles in neat trifluoroacetic acid (TFA); (2) a Pd(OAc)₂ (10 mol %) or CuI (10 mol %) mediated nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar₃P)₃ [Ar = 3,5-(F₃C)₂C₆H₃] [aka Superstable Pd(0) Catalyst] (10 mol %) mediated intramolecular C-N cyclization of 3-(2-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitriles. All new compounds are fully characterized.

Original language	English
Pages (from-to)	8329-8340
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	80
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.5b01514
Publication status	Published - 21 Aug 2015

Access to Document

10.1021/acs.joc.5b01514

Cite this

@article{54a82e3c56d54bcb83737bd79269733c,

title = "The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings",

abstract = "Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared in high yields via three new routes: (1) a Cu(OTf)2 (0-5 mol \%) catalyzed hypervalent iodine [PhI(OTf)2] mediated oxidative coupling of 4-anilinoquinazoline-2-carbonitriles in neat trifluoroacetic acid (TFA); (2) a Pd(OAc)2 (10 mol \%) or CuI (10 mol \%) mediated nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar3P)3 [Ar = 3,5-(F3C)2C6H3] [aka Superstable Pd(0) Catalyst] (10 mol \%) mediated intramolecular C-N cyclization of 3-(2-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitriles. All new compounds are fully characterized.",

author = "Mirallai, \{Styliana I.\} and Koutentis, \{Panayiotis A.\}",

year = "2015",

month = aug,

day = "21",

doi = "10.1021/acs.joc.5b01514",

language = "English",

volume = "80",

pages = "8329--8340",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "16",

}

The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings. / Mirallai, Styliana I.; Koutentis, Panayiotis A.
In: Journal of Organic Chemistry, Vol. 80, No. 16, 21.08.2015, p. 8329-8340.

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

TY - JOUR

T1 - The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings

AU - Mirallai, Styliana I.

AU - Koutentis, Panayiotis A.

PY - 2015/8/21

Y1 - 2015/8/21

N2 - Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared in high yields via three new routes: (1) a Cu(OTf)2 (0-5 mol %) catalyzed hypervalent iodine [PhI(OTf)2] mediated oxidative coupling of 4-anilinoquinazoline-2-carbonitriles in neat trifluoroacetic acid (TFA); (2) a Pd(OAc)2 (10 mol %) or CuI (10 mol %) mediated nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar3P)3 [Ar = 3,5-(F3C)2C6H3] [aka Superstable Pd(0) Catalyst] (10 mol %) mediated intramolecular C-N cyclization of 3-(2-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitriles. All new compounds are fully characterized.

AB - Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles are prepared in high yields via three new routes: (1) a Cu(OTf)2 (0-5 mol %) catalyzed hypervalent iodine [PhI(OTf)2] mediated oxidative coupling of 4-anilinoquinazoline-2-carbonitriles in neat trifluoroacetic acid (TFA); (2) a Pd(OAc)2 (10 mol %) or CuI (10 mol %) mediated nonoxidative coupling of 4-(2-bromoanilino)quinazoline-2-carbonitrile; and (3) a nonoxidative Pd(Ar3P)3 [Ar = 3,5-(F3C)2C6H3] [aka Superstable Pd(0) Catalyst] (10 mol %) mediated intramolecular C-N cyclization of 3-(2-bromophenyl)-4-imino-3,4-dihydroquinazoline-2-carbonitriles. All new compounds are fully characterized.

UR - https://www.scopus.com/pages/publications/84940062555

U2 - 10.1021/acs.joc.5b01514

DO - 10.1021/acs.joc.5b01514

M3 - Article

AN - SCOPUS:84940062555

SN - 0022-3263

VL - 80

SP - 8329

EP - 8340

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

The Conversion of 4-Anilinoquinazoline- and 3-Aryl-4-imino-3,4-dihydro-quinazoline-2-carbonitriles into Benzo[4,5]imidazo[1,2-c]quinazoline-6-carbonitriles via Oxidative and Nonoxidative C-N Couplings

Abstract

Access to Document

Other files and links

Fingerprint

Cite this