Synthetic approaches to 2‐substituted 1‐oxo‐ and 3‐oxotetrahydroisoquinolines

Chen‐Yu ‐Y Cheng, Hui‐Bing ‐B Tsai, Mei‐Shan ‐S Lin

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

2‐Substituted homophthalimides 2a‐c were reduced regioselectively with sodium borobydride to carbinol‐lactam intermediates 3a‐c, which were dehydrated, followed by hydrogenation, to give 1‐oxo‐tetrabydroisoquinolines or 3,4‐dihydroisoquinolin‐1(2H)ones 5a‐c. The isomeric 3‐oxo‐tetrahydro‐isoquinolines or 1,4‐dihydroisoquinolin‐3(2H)‐ones 8a‐i were obtained in satisfactory yields via heating 3‐isochromanone (6) with the corresponding amines 7a‐i in the presence of aluminum chloride.

Original languageEnglish
Pages (from-to)73-77
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume32
Issue number1
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

Fingerprint

Hydrogenation
Amines
Sodium
Heating
aluminum chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic approaches to 2‐substituted 1‐oxo‐ and 3‐oxotetrahydroisoquinolines. / Cheng, Chen‐Yu ‐Y; Tsai, Hui‐Bing ‐B; Lin, Mei‐Shan ‐S.

In: Journal of Heterocyclic Chemistry, Vol. 32, No. 1, 01.01.1995, p. 73-77.

Research output: Contribution to journalArticle

@article{6227432969aa407a9e5685d078024795,
title = "Synthetic approaches to 2‐substituted 1‐oxo‐ and 3‐oxotetrahydroisoquinolines",
abstract = "2‐Substituted homophthalimides 2a‐c were reduced regioselectively with sodium borobydride to carbinol‐lactam intermediates 3a‐c, which were dehydrated, followed by hydrogenation, to give 1‐oxo‐tetrabydroisoquinolines or 3,4‐dihydroisoquinolin‐1(2H)ones 5a‐c. The isomeric 3‐oxo‐tetrahydro‐isoquinolines or 1,4‐dihydroisoquinolin‐3(2H)‐ones 8a‐i were obtained in satisfactory yields via heating 3‐isochromanone (6) with the corresponding amines 7a‐i in the presence of aluminum chloride.",
author = "Cheng, {Chen‐Yu ‐Y} and Tsai, {Hui‐Bing ‐B} and Lin, {Mei‐Shan ‐S}",
year = "1995",
month = "1",
day = "1",
doi = "10.1002/jhet.5570320113",
language = "English",
volume = "32",
pages = "73--77",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "1",

}

TY - JOUR

T1 - Synthetic approaches to 2‐substituted 1‐oxo‐ and 3‐oxotetrahydroisoquinolines

AU - Cheng, Chen‐Yu ‐Y

AU - Tsai, Hui‐Bing ‐B

AU - Lin, Mei‐Shan ‐S

PY - 1995/1/1

Y1 - 1995/1/1

N2 - 2‐Substituted homophthalimides 2a‐c were reduced regioselectively with sodium borobydride to carbinol‐lactam intermediates 3a‐c, which were dehydrated, followed by hydrogenation, to give 1‐oxo‐tetrabydroisoquinolines or 3,4‐dihydroisoquinolin‐1(2H)ones 5a‐c. The isomeric 3‐oxo‐tetrahydro‐isoquinolines or 1,4‐dihydroisoquinolin‐3(2H)‐ones 8a‐i were obtained in satisfactory yields via heating 3‐isochromanone (6) with the corresponding amines 7a‐i in the presence of aluminum chloride.

AB - 2‐Substituted homophthalimides 2a‐c were reduced regioselectively with sodium borobydride to carbinol‐lactam intermediates 3a‐c, which were dehydrated, followed by hydrogenation, to give 1‐oxo‐tetrabydroisoquinolines or 3,4‐dihydroisoquinolin‐1(2H)ones 5a‐c. The isomeric 3‐oxo‐tetrahydro‐isoquinolines or 1,4‐dihydroisoquinolin‐3(2H)‐ones 8a‐i were obtained in satisfactory yields via heating 3‐isochromanone (6) with the corresponding amines 7a‐i in the presence of aluminum chloride.

UR - http://www.scopus.com/inward/record.url?scp=0028952202&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028952202&partnerID=8YFLogxK

U2 - 10.1002/jhet.5570320113

DO - 10.1002/jhet.5570320113

M3 - Article

VL - 32

SP - 73

EP - 77

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 1

ER -