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Title:
CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2013/132520
Kind Code:
A4
Abstract:
The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocinnamonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.

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Inventors:
AHUJA BRIJ BHUSHAN (IN)
REKULA REDDY SANTOSH (IN)
SUDALAI ARUMUGAM (IN)
Application Number:
PCT/IN2013/000137
Publication Date:
October 31, 2013
Filing Date:
March 07, 2013
Export Citation:
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Assignee:
COUNCIL SCIENT IND RES (IN)
International Classes:
C07D317/60; C07C253/14; C07C303/30; C07C319/20
Attorney, Agent or Firm:
DHAWAN, Ramesh, Chander (Plot No. B- 28 Sector - 32,Institutional Area, Gurgaon - 1, IN)
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Claims:
AMENDED CLAIMS

received by the International Bureau on 10 September 2013(10.09.2013)

We claim:

1. A one pot, single step process for the preparation of compound of general formula A and its isomers,

Formula A

starting from compounds of formula I,

Formula I,

wherein,

R1 is hydrogen;

R2 is selected from H, OMe, OTs, Obn;

R3 is selected from H, OMe, OTs, OBn, N02;

R* is selected from H, OMe, F;

R5 is selected from H, N02, BR;

R5' is selected from H, N02, CN;

R* and R3 can together be selected as -0-CH.-0-;

comprising the steps of reacting compound of formula I with CuCN in DMF, under reflux in presence of atmosphere to obtain the desired compound of Formula A in the range of 50% -90% yield.

2. The process according to claim 1, wherein said compound of formula I and CuCN are in the ratio of 1:2 to 1:3.

3. The process according to claim 1, wherein said isomers of compound of formula A are trans and cis isomers in the ratio of 3: 1 to 10:1.

4. The process according to claim 1, wherein the reaction is carried out at a temperature ranging from 140 to 160 °C.

5. The process according to claim 1, wherein the reaction is carried out for a time ranging from 10 to 15 hours.