Junjappa-ila annulation

α-oxoketene dithioacetal mediated synthesis of substituted benzotriazoles

Nitinkumar S. Shetty, Ravi S. Lamani, Shridhar I. Panchamukhi, Imtiyaz Ahmed M Khazi

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 2-(1-Benzyl-1H-1,2,3-triazole-4-yl)-3- methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile 3a-e were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile (1) with various α-oxoketene dithioacetals 2a-e in the presence of sodium hydride. The intermediates 3a-e underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a-e in moderate yields.

Original languageEnglish
Pages (from-to)774-777
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume46
Issue number4
DOIs
Publication statusPublished - 07-2009

Fingerprint

Triazoles
Cyclization
Condensation
Acids
benzotriazole
acetonitrile
sodium hydride
1,3,6,8-pyrene tetrasulfonate

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Shetty, Nitinkumar S. ; Lamani, Ravi S. ; Panchamukhi, Shridhar I. ; Khazi, Imtiyaz Ahmed M. / Junjappa-ila annulation : α-oxoketene dithioacetal mediated synthesis of substituted benzotriazoles. In: Journal of Heterocyclic Chemistry. 2009 ; Vol. 46, No. 4. pp. 774-777.
@article{e399959428f342f0a245c8a3bf42c021,
title = "Junjappa-ila annulation: α-oxoketene dithioacetal mediated synthesis of substituted benzotriazoles",
abstract = "(Chemical Equation Presented) 2-(1-Benzyl-1H-1,2,3-triazole-4-yl)-3- methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile 3a-e were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile (1) with various α-oxoketene dithioacetals 2a-e in the presence of sodium hydride. The intermediates 3a-e underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a-e in moderate yields.",
author = "Shetty, {Nitinkumar S.} and Lamani, {Ravi S.} and Panchamukhi, {Shridhar I.} and Khazi, {Imtiyaz Ahmed M}",
year = "2009",
month = "7",
doi = "10.1002/jhet.85",
language = "English",
volume = "46",
pages = "774--777",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "4",

}

Junjappa-ila annulation : α-oxoketene dithioacetal mediated synthesis of substituted benzotriazoles. / Shetty, Nitinkumar S.; Lamani, Ravi S.; Panchamukhi, Shridhar I.; Khazi, Imtiyaz Ahmed M.

In: Journal of Heterocyclic Chemistry, Vol. 46, No. 4, 07.2009, p. 774-777.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Junjappa-ila annulation

T2 - α-oxoketene dithioacetal mediated synthesis of substituted benzotriazoles

AU - Shetty, Nitinkumar S.

AU - Lamani, Ravi S.

AU - Panchamukhi, Shridhar I.

AU - Khazi, Imtiyaz Ahmed M

PY - 2009/7

Y1 - 2009/7

N2 - (Chemical Equation Presented) 2-(1-Benzyl-1H-1,2,3-triazole-4-yl)-3- methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile 3a-e were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile (1) with various α-oxoketene dithioacetals 2a-e in the presence of sodium hydride. The intermediates 3a-e underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a-e in moderate yields.

AB - (Chemical Equation Presented) 2-(1-Benzyl-1H-1,2,3-triazole-4-yl)-3- methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile 3a-e were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile (1) with various α-oxoketene dithioacetals 2a-e in the presence of sodium hydride. The intermediates 3a-e underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a-e in moderate yields.

UR - http://www.scopus.com/inward/record.url?scp=67749124385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67749124385&partnerID=8YFLogxK

U2 - 10.1002/jhet.85

DO - 10.1002/jhet.85

M3 - Article

VL - 46

SP - 774

EP - 777

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 4

ER -