کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1343729 1500342 2015 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
7-endo cyclization of 2,3-epoxyamides and 2,3-aziridine carboxamides by intramolecular Friedel–Crafts reaction
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
7-endo cyclization of 2,3-epoxyamides and 2,3-aziridine carboxamides by intramolecular Friedel–Crafts reaction
چکیده انگلیسی

A high yielding regio- and diastereoselective 7-endo 2,3-epoxyamides and 2,3-aziridine carboxamide cyclization is reported. Several aryl and alkyl trans-2,3-epoxyamides were reacted with BF3·OEt2 to afford the corresponding 4-hydroxy-5-alkyl/aryl-tetrahydro-2-benzazepin-3-ones. In addition, arene cyclization with aryl 2,3-aziridine carboxamides was investigated.

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(3R,6R,7S,11bR)-6-Hydroxy-7-phenyl-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC21H23NO3[α]D20 = +105.0 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

(3R,6R,7S,11bR)-6-Hydroxy-7-(2-nitrophenyl)-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC21H22N2O5[α]D20 = −134.1 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

(3R,6R,7S,11bR)-6-Hydroxy-7-(3-nitrophenyl)-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC21H22N2O5[α]D20 = +32.4 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

(3R,6R,7S,11bR)-6-Hydroxy-7-(4-nitrophenyl)-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC21H22N2O5[α]D20 = +104.3 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3′R,6R,7S,11bR)

(3R,6R,7R,11bR)-6-Hydroxy-7-(2,6-dichlorophenyl)-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC21H21Cl2NO3[α]D20 = +87.2 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7R,11bR)

(3R,6R,7S,11bR)-6-Hydroxy-7-methyl-3-propyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC16H21NO3[α]D20 = −33.3 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

(3R,6R,7S,11bR)-6-Hydroxy-3,7-dipropyl-1,6,7,11b-tetrahydrobenzo[c]oxazolo[3,4-a]azepin-5(3H)-oneC18H25NO3[α]D20 = +10.1(c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

(1R,4R,5S)-4-Hydroxy-1-(hydroxymethyl)-5-isopropyl-4,5-dihydro-1H-benzo[c]azepin-3(2H)-oneC14H19NO3[α]D20 = −18.5 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (1R,4R,5S)

4-Methyl-N-((3R,6R,7S,11bR)-5-oxo-7-phenyl-3-propyl-1,3,5,6,7,11b-hexahydrobenzo[c]oxazolo-[3,4-a]azepin-6-yl)benzenesulfonamideC28H30N2O4S[α]D20 = +13.8 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

4-Methyl-N-((3R,6R,7R,11bR)-5-oxo-7-phenyl-3-propyl-1,3,5,6,7,11b-hexahydrobenzo[c]oxazolo[3,4-a]azepin-6-yl)benzenesulfonamideC28H30N2O4S[α]D20 = +20.9 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7R,11bR)

4-Methyl-N-((3R,6R,7S,11bR)-7-(4-nitrophenyl)-5-oxo-3-propyl-1,3,5,6,7,11b-hexahydrobenzo[c]oxazolo[3,4-a]azepin-6-yl)benzenesulfonamideC28H29N3O6S[α]D20 = +107.6 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

N-((3R,6R,7S,11bR)-7-(3,5-Dichlorophenyl)-5-oxo-3-propyl-1,3,5,6,7,11b-hexahydrobenzo[c]oxazolo[3,4-a]azepin-6-yl)-4-methylbenzenesulfonamideC28H28Cl2N2O4S[α]D20 = +21.0 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7S,11bR)

N-((3R,6R,7R,11bR)-7-(3,5-Dichlorophenyl)-5-oxo-3-propyl-1,3,5,6,7,11b-hexahydrobenzo[c]oxazolo[3,4-a]azepin-6-yl)-4-methylbenzenesulfonamideC28H28Cl2N2O4S[α]D20 = −223.7 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (3R,6R,7R,11bR)

(1R,4R,5S)-2-Butyl-1-(hydroxymethyl)-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-olC21H27NO2[α]D20 = −23.2 (c 1.0, CH2Cl2)Source of chirality: (R)-(−)-2-phenylglycinolAbsolute configuration: (1R,4R,5S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 26, Issues 2–3, 15 February 2015, Pages 95–101
نویسندگان
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