Aminol initiated Prins cyclization for the synthesis of octahydro-1H-pyrano [3,4-c]pyridine and hexahydro-1H-furo[3,4-c]pyrrole derivatives

Reddy, B. V. Subba; Reddy, S. Gopal; Reddy, M. Ramana; Sridhar, Balasubramanian; Bhadra, Manika Pal

doi:10.1016/j.tetlet.2014.06.109

Cited by 10 publications

(2 citation statements)

References 30 publications

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“…Many drugs used in medical practice have a complex structure containing a pyranopyridine ring, such as camptothecin, irinotecan, topotecan, and others. Pyrano[3,4‐ c ]pyridines, which are extracted from plants, are endowed with universal biological action, but synthetic methods to obtain them are limited [1–3].…”

Section: Introductionmentioning

confidence: 99%

One‐pot effective synthesis of new heterocyclic system: Pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one

Harutyunyan

Dashyan

Shahkhatuni

2022

Journal of Heterocyclic Chem

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One‐pot effective methods for the synthesis of derivatives of 6‐amino‐3,3‐dimethyl‐7‐aryl substituted‐8‐thioxo(oxo)‐pyrano[3,4‐c]pyridineswere developed. The proposed mechanisms of one‐pot reactions are presented. The derivatives of 8‐oxo‐pyrano[3,4‐c]pyridines served as starting materials for the synthesis of a new heterosystem—pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one. The antimicrobial activity of the obtained compounds was studied.

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Section: Introductionmentioning

confidence: 99%

One‐pot effective synthesis of new heterocyclic system: Pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one

Harutyunyan

Dashyan

Shahkhatuni

2022

Journal of Heterocyclic Chem

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“…These resultsc learly indicate that the newly discovered cyclization to form the 3,5,6,7-tetrahydro-1H-pyrano [3,4-c]pyridine skeleton strictly requires an ynamide-based 1,3,8-triynef ramework bearing an appropriate hydride-or hydrogen-donating functionality. [9] Otherwise, no reactiono rd ifferent types of thermalr eactions of the multiply unsaturated framework outcompetetogenerate products of alternative cyclizations.…”

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confidence: 99%

Cyclization of Ynamide‐Tethered 1,3,8‐Triynes

Sabbasani

Lee

Xie

et al. 2017

Chemistry A European J

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A facile thermal cyclization of ynamide-tethered 1,3,8-triynes to form a 3,5,6,7-tetrahydro-1H-pyrano[3,4-c]pyridine skeleton is described. Although the mechanism of this unusual reaction has yet to be defined, the formation of either a strained keteniminium or a biradical intermediate followed by a 1,5-hydride or -hydrogen shift is tentatively proposed as the key elementary steps in the reaction sequence. Appropriate electronic activation at the carbon center donating a hydride or hydrogen is crucial for successful cyclization.

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Reactions of Aldehydes and Ketones and their Derivatives

Murray

2017

Organic Reaction Mechanisms · 2014

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Aminol initiated Prins cyclization for the synthesis of octahydro-1H-pyrano [3,4-c]pyridine and hexahydro-1H-furo[3,4-c]pyrrole derivatives

Cited by 10 publications

References 30 publications

One‐pot effective synthesis of new heterocyclic system: Pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one

One‐pot effective synthesis of new heterocyclic system: Pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one

Cyclization of Ynamide‐Tethered 1,3,8‐Triynes

Reactions of Aldehydes and Ketones and their Derivatives

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